Tag: M.W=200-300

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 90347-66-3 as follows. COA of Formula: C9H9IO2

To the oil of Step 1 in THF, copper iodide (1.1 g, 5.74 mmol, 0.1 eq) and tetrakis (triphenylphosphine) palladium (3.3 g, 2.86 mmol, 0.05 eq) was added. The solution was purged with nitrogen 3 times. To the solution triethylamine (11.57 g, 114.28 mmol, 2.0 eq) and trimethylsilylacetylene (8.4 g, 85.71 mmol, 1.5 eq) was added. Then the solution obtained was stirred at room temperature for 24 hours, evaporated to dryness under reduced pressure and the title product was isolated by column chromatography as a yellow oil.

According to the analysis of related databases, 90347-66-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Si Chuan University; Yang, Shengyong; Wei, Yuquan; (168 pag.)US2017/305920; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 191348-14-8, name is 2-Iodo-4-methoxyaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 2-Iodo-4-methoxyaniline

Under anhydrous and anaerobic conditions, 0.1 mmol of 2-iodo-4-methoxyaniline, 0.12 mmol of 3-fluoro-4-methoxybenzaldehyde, 0.3 mmol of selenium powder, 0.005 mmol of copper, 0.2 mmol of potassium hydroxide and 10 ml were added. DMSO solution in a single-mouth round bottom flaskIn the reflux reaction at 120 C, the reaction was monitored by TLC, and the pure methoxy-containing benzoselenazole compound was obtained by column chromatography.The product was demethylated with boron tribromide (6 eq.) to give the product as a white solid.The yield was 28%.

The synthetic route of 2-Iodo-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuhan University; Zhou Haibing; Zhang Silong; Hu Zhiye; Li Yuanyuan; Ning Wentao; Dong Chune; (13 pag.)CN108863985; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 25309-64-2,Some common heterocyclic compound, 25309-64-2, name is 1-Ethyl-4-iodobenzene, molecular formula is C8H9I, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A 250 mL 3 -neck round bottom flask equipped with a thermometer and a magnetic stirring bar was charged with 4.01 g (61.3 mmol) of zinc dust and 35 mL of dimethylformamide (DMF) under a nitrogen atmosphere. The slurry was treated with 0.56 g (2.2 mmol) of iodine. The red disappeared in 90 seconds. The reaction mixture was treated with 6.00 mL (8.18 g, 42.0 mmol) of ethyl 4-bromobutyrate and heated to 800C for 4 hour. The reaction mixture was cooled to 300C and treated with 4.98 g (21.5 mmol) of 4-iodoethylbenzene and 0.48 g (0.9 mmol) of dichlorobis(triphenylphosphine)nickel(II). The reaction mixture was heated to 45C for 80 hours. The cooled reaction mixture was treated with aqueous 4% hydrochloric acid to quench the excess zinc. The mixture was extracted with methyl t-butyl ether (MTBE) (1 X 60 mL). The organic phase was washed with brine (1 X 30 mL), dried over sodium sulfate and concentrated. The crude ethyl 4-(4-ethylphenyl)butyrate was taken up in ethanol, treated with 20 mL of 2N aqueous sodium hydroxide, and heated to reflux. After 4 hours the reaction mixture was cooled to 25C and washed with MTBE (2 X 30 mL). The aqueous phase was acidified with aqueous 4% hydrochloric acid. A solid was isolated by filtration to give 1.99 g of 4-(4-ethylphenyl)butanoic acid. IH NMR (d6- DMSO): delta 11.9, bs, IH (COOH); delta 6.98, d, 2H, (arylH’s); delta 6.95, d, 2H (arylH’s); delta 2.41, m, 4H, (CH2’s alpha to aryl); delta 2.07, t, 2H (CH2 alpha to COOH); delta 1.64, m, 2H (CH2 beta to both aryl and COOH); delta 1.03, t, 3H (CH3). 13C NMR (d6-DMSO): 174.23, 141.08, 138.67, 128.20, 127.65, 33.97, 33.03, 27.73, 26.35, 15.65.

The synthetic route of 25309-64-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EMISPHERE TECHNOLOGIES, INC.; WO2008/112368; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 25309-64-2, These common heterocyclic compound, 25309-64-2, name is 1-Ethyl-4-iodobenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a stirred solution of aryl halides (2.0 mmol) and thiourea (1.2 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 110 C for 15 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (20 mL) was added. The combined organic extracts were dried with anhydrous Na2SO4. The solvent and volatiles were completely removed under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 9:1) to afford the corresponding coupling product in excellent yields.Recycling of the catalyst:after the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (2.0 mL) was added and CuO was removed by centrifugation. After each cycle, the catalyst was recovered by simple centrifugation, washing with deionized water and ethyl acetate and then drying in vacuo. The recovered nano CuO was used directly in the next cycle.Data of representative examples:Dip-tolylsulfane (Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Bis(4-ethylphenyl)sulfane (Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Bis(3-nitrophenyl)sulfane (Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.4,4′-Thiodianiline (Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Dithiophen-3-ylsulfane (Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Dipyrimidin-5-ylsulfane (Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; found: C, 50.45; H, 3.13; N, 29.41; S, 16.81.Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; f…

Statistics shows that 1-Ethyl-4-iodobenzene is playing an increasingly important role. we look forward to future research findings about 25309-64-2.

Reference:
Article; Reddy, K. Harsha Vardhan; Reddy, V. Prakash; Shankar; Madhav; Anil Kumar; Nageswar; Tetrahedron Letters; vol. 52; 21; (2011); p. 2679 – 2682;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 5326-39-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5326-39-6, name is 1-Iodo-4-methyl-2-nitrobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of i-1 (1-Iodo-4-methyl-2-nitro-benzene, 0. 0038 mol), methyl-vinylketone (0.0076 mol), Et3N (0.0076 mol) and Pd (OAc) 2 (0.00019 mol) in CH3CN (6 ml) were stirred in a microwave oven (100C, 100 W) for 5 min. The reaction was then filtered through a pad of celite and the filtrate was concentrated. The residue was purified by column chromatography over silica gel (eluent: CH2Cla/Cyclohexane 70/30). Yield: 0.65 g of i-2 (4- (4-Methyl-2-nitro-phenyl)-but-3-en-2-one, 78%, melting point: 58C).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Iodo-4-methyl-2-nitrobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2005/58871; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 4949-69-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4949-69-3, name is 4-Iodo-3-methylaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-iodo-5-aminotoluene (10 g, 43.1 mmol) in THF (200 ml) was added sodium bicarbonate (10.81 g, 128.76 mmol) and Boc2O (14.09 g, 64.66 mmol) and the reaction mixture was stirred at 50 C for 12 h. The reaction mixture was then cooled to room temperature, filtered and concentrated under reduced pressure. The residue was partitioned between brine and AcOEt and the aqueous layer was extracted with AcOEt. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give 10 g (yield 69%) of brown solid corresponding to tert-butyl 4-iodo-3-methylphenylcarbamate. The crude product was used in the next step without further purification. Mass: (ES+) C12H16INO2 required 333.02; found 332 [M-H], HPLC/MS method 4.

The synthetic route of 4-Iodo-3-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENOSCIENCE PHARMA; BRUN, Sonia; BERET, Antoine; BASSISSI, Firas; HALFON, Philippe; COURCAMBECK, Jerome; (275 pag.)WO2017/191599; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 13421-00-6, A common heterocyclic compound, 13421-00-6, name is 5-Chloro-2-iodobenzoic acid, molecular formula is C7H4ClIO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Reference Example 2-66 5-Chloro-2-[[1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid Following the procedure described in Reference Example 2-5, the title compound was prepared from 5-chloro-2-iodobenzoic acid and 1-(2-pyridinyl)-1H-pyrazol-5-ylamine (88% yield). mp: 233-234 C. (recrystallized from ethanol). NMR (DMSO-d6) delta: 6.42 (1H, d, J=2.0 Hz), 7.38 (1H, ddd, J=1.2 Hz, 4.8 Hz, 7.4 Hz), 7.54 (1H, dd, J=2.6 Hz, 8.8 Hz), 7.63 (1H, d, J=8.8 Hz), 7.71 (1H, d, J=2.0 Hz), 7.88-7.92 (2H, m), 7.99-8.08 (1H, m), 8.47 (1H, dd, J=0.8 Hz, 1.8 Hz, 4.8 Hz), 12.24 (1H, br s), hidden (1H).

The synthetic route of 13421-00-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Uchikawa, Osamu; Mitsui, Keita; Asakawa, Akiko; Morimoto, Shigeru; Yamamoto, Masataka; Kimura, Hiroyuki; Moriya, Takeo; Mizuno, Masahiro; US2003/187014; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 887266-99-1,Some common heterocyclic compound, 887266-99-1, name is 3-Fluoro-4-iodobenzonitrile, molecular formula is C7H3FIN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a mixture of tert- butyl (S)-7,l0-dioxo-6-(4-(trifluoromethyl)benzyl)-2,6,9- triazaspiro[4.5]decane-2-carboxylate (280 mg, 0.63 mmol), Cul (60 mg, 0.32 mmol, 0.5 equiv.), K2CO3 (349 mg, 2.53 mmol, 4.0 equiv.) and aryl iodide (234 mg, 0.95 mmol, 1.5 equiv.) in l,4-dioxane (6 mL) was added N,N-dimethylethylenediamine (0.034 mL, 0.32 mmol, 0.5 equiv.). The resulting mixture was heated at 115 C under N2 for 18 h in a sealed tube, cooled to r.t, filtered through celite, washed with additional dioxane (15 mL) and DCM (30 mL), concentrated under reduced pressure, and purified by silica gel chromatography using EA / Hex (1/1) as eluents to provide 187 mg (54%) of tert-butyl (S)-9-(4-cyano-2- fluorophenyl)-7,l0-dioxo-6-(4-(trifluoromethyl)benzyl)-2,6,9-triazaspiro[4.5]decane-2- carboxylate. LRMS (APCI) m/z 491.1 (M+H) (-C4H9). NMR (400 MHz, Methanol-i/4) d 7.82 – 7.64 (m, 5H), 7.50 (d, J = 8.0 Hz, 2H), 5.15 – 5.02 (m, 1H), 4.81 – 4.57 (m, 3H), 4.00 (d, J = 12.1 Hz, 1H), 3.66 (d, J = 12.3 Hz, 1H), 3.62 – 3.47 (m, 2H), 2.59 – 2.48 (m, 2H),

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Fluoro-4-iodobenzonitrile, its application will become more common.

Reference:
Patent; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; ASHCRAFT, Luke W.; LAU, Kevin; (455 pag.)WO2020/47447; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 82998-57-0 as follows. Quality Control of 3-Iodo-4-methylbenzoic acid

To a solution of 3-iodo-4-methyl-benzoic acid (10.0 g, 38.2 mmol) in methanol (70 ml) is added concentrated sulfuric acid (0.5 ml). The reaction mixture is heated at 70 C. for 48 hours, cooled to room ambient temperature and then concentrated. After that, ethyl acetate (100 ml) and aqueous NaHCO3 (saturated, 100 ml) solution are added to the residue. The organic layer is separated and washed again with aqueous NaHCO3 (saturated, 100 ml) solution. The organic layer is separated, dried over anhydrous Na2SO4 and concentrated to yield 3-iodo-4-methyl-benzoic acid methyl ester 1. It is used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) delta 8.31 (s, 1H), 7.87 (d, 1H, J=8.4 Hz), 7.48 (d, 1H, J=8.4 Hz), 3.85 (s, 3H), 3.35 (s, 3H); LC-MS m/z: 277.0 (M+1).

According to the analysis of related databases, 82998-57-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; US2009/203666; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 103962-05-6,Some common heterocyclic compound, 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, molecular formula is C7H4F3IO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 2. 4-[l-(4-Trifluoromethoxyphenyl)-lH-[l,2,4]triazol-3-yl]-benzonitrile.. The triazole (70 mg, 0.41 mmol), l-iodo-4-trifluoromethoxybenzene (142 mg, 0.493 mmol), Cs2CO3 (535 mg, 1.644 mmol), CuI (3 mg, 0.012 mmol), 8-hydroxyquinoline (2 mg, 0.012 mmol), and DMF/Eta2O (2 mL; 10:1 solution) were combined in a 10 mL CEM Microwave reaction vessel fitted with magnetic stir bar and subjected to microwave irradiation at 150 0C for 30 min. The contents were then filtered and concentrated to dryness affording the 1,3- diphenyl triazole intermediate (18 mg, 13percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-4-(trifluoromethoxy)benzene, its application will become more common.

Reference:
Patent; DOW AGROSCIENCES LLC; LAMBERT, William; CROUSE, Gary; SPARKS, Thomas; CUDWORTH, Denise; WO2011/17513; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com