Tag: M.W=200-300

Electric Literature of 52548-63-7,Some common heterocyclic compound, 52548-63-7, name is 5-Fluoro-2-iodobenzoic acid, molecular formula is C7H4FIO2, 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 solution of 3-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-pyrrolo[2,3-c]pyridine (9.0 g, 34.84 mmol) in 200 mL of anhydrous DMF was added 5-fluoro-2-iodobenzoic acid (9.3 g, 34.84 mmol), Cu (442 mg, 6.97 mmol) and K2CO3 (14.4 g, 104.52 mmol). The resulting mixture was degassed and purged with N2 3 times, then stirred at 130 oC for 24 h under N2. The reaction mixture was then filtered through celite. The filtered cake was washed with EtOAc (150 mL) and the filtrate was concentrated under reduced pressure to remove most of the EtOAc and DMF. The resulting residue was poured into water (300 mL). The aqueous layer was adjusted by 6 N HCl to pH = 6-7, extracted with EtOAc (3 × 300 mL), and some white precipitate was formed. The suspension was then filtered. The filtered cake was collected and dried under reduced pressure to give a first batch of 2-(3- (1,4-dioxaspiro[4.5]decan-8-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)-5-fluorobenzoic acid (7.5 g) as white solid. The organic layers was washed with brine (3 × 300 mL), then dried over anhydrous Na2SO4, filtered and filtrate was concentrated under reduced pressure to give a second batch of 2-(3-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-pyrrolo[2,3-c]pyridin-1- yl)-5-fluorobenzoic acid (4.5 g) as brown solid. Yield: 12.0 g (87%); LCMS method E: Rt = 0.649 min; (M+H)+ = 397.0.1H NMR (DMSO-d6): delta ppm 8.45 (s, 1H), 8.20-8.22 (d, J = 5.6, 1H), 7.60-7.80 (m, 4H), 7.53 (s, 1H), 3.95 (4, 1H), 2.90-3.00 (m, 1H), 2.03-2.10 (m, 2H), 1.65-1.85 (m, 6H).19F NMR (DMSO-d6): delta ppm -112.83.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Fluoro-2-iodobenzoic acid, its application will become more common.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David A.; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen D.; SINGH, Suresh B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; (285 pag.)WO2018/53267; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 191348-14-8, name is 2-Iodo-4-methoxyaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 191348-14-8

Under anhydrous and anaerobic conditions, 0.1 mmol of 2-iodo-4-methoxyaniline was added.0.12 mmol of 2,5-dimethoxybenzaldehyde, 0.3 mmol of selenium powder,0.005 mmol of copper, 0.2 mmol of potassium hydroxide and 10 ml of DMSO solution were refluxed at 120 C in a single-neck round bottom flask, and the reaction was monitored by TLC.Separation of pure methoxy-containing benzoselenazole compounds by column chromatographyThe reaction product is obtained by demethylation of boron tribromide (6 eq.),The product is a white solid.The yield was 21%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

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

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. 153898-63-6, name is 2-Iodo-5-methoxyaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2-Iodo-5-methoxyaniline

The intermediate 3- (3-isopropyl-4-methoxybenzylamino) -1- (3,4,5-trimethoxyphenyl) acetone-2-ynyl (3) (0.20g, 0.52mmol ), 2-iodo-5-methoxyaniline (4) (0.16g, 0.62mmol) was dissolved in dry methanol and a mixture of anhydrous DMSO (1.5), an argon atmosphere, was stirred at 120 60h.After the reaction, by column chromatography (Pe / EtOAc = 7:1) to give a yellow solid intermediate.This intermediate was dissolved in dry of DMF, palladium acetate (11.6mg, 0.052mmol), triethylamine (0.21g, 2.08mmol), stirred for an argon atmosphere 120 14h.After the reaction, by column chromatography (Pe / EtOAc = 5:1) to give a yellow solid, a 2- (4′-methoxy-3′-isopropoxy-phenyl) -3- (3 “, 4”, 5 ‘- trimethoxy-benzoyl) -6-methoxy-indole (5) (131.4mg, the yield 50%).. 1HNMR (500 MHz, CDCl33)delta8.61(s1H)7.93(dJ9.3Hz1H)6.99(s3H)6.91(ddJ4.72.4Hz2H)6.75(ddJ5.03.1Hz2H)4.17(dtJ12.26.1Hz1H)3.86(s3H)3.79(s6H)3.67(s6H)1.20(dJ6.1Hz6H).13C NMR(126MHzCDCl3)delta191.9157.5152.7151.2147.4142.4141.4136.5134.7125.0123.4122.6121.1117.5112.9111.8107.594.771.960.956.155.929.822.1.ESI-MS[M+H]+506.2[M+Na]+528.4.HRMS(ESI)m/z calcd for C29H31NO7[M+H]+506.2173found506.2158

The synthetic route of 153898-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong YizhengdaMedical Technology Co Ltd; Sun, Qing; Zhang, Weidong; (13 pag.)CN104262229; (2016); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 13329-40-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 13329-40-3 name is 1-(4-Iodophenyl)ethanone, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 32A 2-Bromo-1-(4-iodo-phenyl)-ethanone To the solution of 1-(4-Iodo-phenyl)-ethanone (Aldrich, 125 g, 508 mmol) in glacial acetic acid (600 mL) was added the bromine (Aldrich, 79.3 g, 508 mmol, in 50 mL of acetic acid) and stirred at room temperature for 10 hours. It was concentrated under reduced pressure. The residue was then diluted with ethyl acetate (100 mL) and washed with brine (3*50 mL). The organic solution was concentrated. The title compound was obtained as yellow solid by recrystallization from diethyl ether (150 g, 91%). 1H NMR (300 MHz, CDCl3) delta 4.39 (s, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.87 (d, J=8.5 Hz, 2H) ppm; MS (DCl/NH3) m/z 246 (M-Br)+, 264 (M-Br+NH4)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Iodophenyl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; Abbott Laboratories; US2005/159597; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 13194-68-8, 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 13194-68-8 as follows.

A solution of NaNO2 (2.96 g, 42.9 mmol) in water (30 mL) was added to a mixture of 4-iodo-2- methyl-aniline (which is available from Aldrich; 5 g, 21.5 mmol) and HC1 (30 mL) at -5 C. Themixture was stilTed at -5 C for 45 mi Tin(II) chloride dihydrate (24.1 g, 107 mmol) was added and the mixture was stirred for 30 mm. The mixture was made alkaline by adding aqueous NaOH solution. The solid was filtered off and purified by chromatography (silica gel) to give (4- iodo-2-methyl-phenyl)-hydrazine (1 g, 19%). ?H NMR (300 MHz, DMSO-d6), oe ppm 7.33 (dd, J=8.5, 2.1 Hz, 1 H), 7.23 (d, J=1.3 Hz, 1 H), 6.87 (d, J=8.5 Hz, 1 H), 6.37 (s, 1 H), 3.98 (s, 2 H),2.01 (s, 3 H, overlapping with CH3 peak from residual EtOAc solvent). MS calcd. for C7H,01N2 ([M+H]j: 249, obsd. 231.8.

According to the analysis of related databases, 13194-68-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHUGAI SEIYAKU KABUSHIKI KAISHA; LOPEZ-TAPIA, Francisco Javier; KONG, Norman; SO, Sung-Sau; LOU, Yan; DOMINIQUE, Romyr; WO2015/86642; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 2265-92-1, 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. 2265-92-1, name is 1,4-Difluoro-2-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A stirred solution of 1 ,4-difluoro-2-iodobenzene (1 .74 g, 7.25 mmol) and 2-(1 – ethynylcyclopropoxy)tetrahydro-2H-pyran (prepared according to the procedure described in J. Am. Chem. Soc, 2009, 131, 9178-9179) (1 .326 g, 7.98 mmol) in diisopropylamine (35 ml) was flushed with argon for 5 min. To this were added bis(triphenylphosphine)palladium(ll) chloride (0.102 g, 0.145 mmol) and copper(l) iodide (0.028 g, 0.145 mmol) and stirring was continued at room temp for 2 hours. The reaction mixture was filtered over kieselguhr, the kieselguhr was washed with ether and the filtrate was concentrated. The residue was partitioned between ethyl acetate (50 ml) and water/sat. NH4CI (aq) (1/1 , 50 ml). After washing, the layers were separated, the organic layer was washed with sat. NaHC03 (50 ml), dried over sodium sulphate and concentrated. The crude product was purified over silica by flash column chromatography ([0% EtOAc in heptane] to [20% EtOAc in heptane]). 1 .89 g (94% of theory) of 2-(1 -((2,5-difluorophenyl)ethynyl)cyclopropoxy)tetrahydro-2H-pyran as a colourless oil was obtained. 1H NMR (CDCIs, 400MHz): 1 .10-1 .22(m,3H,3xCH), 1 .39-1 .43(m,1 H,CH), 1 .51-1 .66(m,4H,2xCH2), 1 .71 -1 .86(m,2H,CH2), 3.57-3.62(m,1 H,0-CH), 3.92-3.97(m,1 Eta,Omicron-CH), 5.12-5.14(m,1 Eta,Omicron-CH-O), 6.92- 7.03(m,2H,Ar-H), 7.05-7.09(m,1 H,Ar-H). MS [M-THP]+ 194

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, 1,4-Difluoro-2-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; STIERLI, Daniel; TITULAER, Ruud; RAJAN, Ramya; WO2014/147009; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 2265-91-0,Some common heterocyclic compound, 2265-91-0, name is 1,3-Difluoro-5-iodobenzene, molecular formula is C6H3F2I, 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 mixture of 8-{[tert-butyl(dimethyl)silyl]oxy}-2-azaspiro[4.5]decan-1-one (isomer 1 ) (425 mg, 1 .50 mmol), 1,3-difluoro-5-iodobenzene (360 mg, 1 .50 mmol, CAS No 2265-91-0), copper(l) iodide (143 mg, 0.750 mmol), N,N’-dimethylethylenediamine (164 muIota, 1 .50 mmol) and potassium carbonate (435 mg, 3.15 mmol) in dioxane (26 ml) was heated to 160 for 2 h in a microwave reactor. Upon cooling, the reaction mixture was filtrated through a pad of celite, and the filtrate was concentrated and the residue was purified by flash chromatography (25 g Snap Cartrige, hexanes/ethyl acetate-gradient, 0% -> 50% ethyl acetate) to give the title compound as single isomer (575 mg).LC-MS (Method 2): Rt= 1 .79 min; MS (ESIpos): m/z = 396.3 [M+H]+1H-NMR (400 MHz, DMSO-d6): delta [ppm] = 7.50-7.41 (m, 2H), 6.98-6.91 (m, 1H), 3.94-3.88 (m, 1H), 3.72 (t, 2H), 2.00-1 .85 (m, 4H), 1 .63-1 .47 (m, 4H), 1 .28-1.20 (m, 2H), 0.85 (s, 9H), 0.01 (s, 6H)

The synthetic route of 2265-91-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; EIS, Knut; WAGNER, Sarah; SUeLZLE, Detlev; VON NUSSBAUM, Franz; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philipp; (248 pag.)WO2018/78005; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 5876-51-7, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5876-51-7, name is 5-Iodobenzo[d][1,3]dioxole, This compound has unique chemical properties. The synthetic route is as follows.

[00215] To 28 mg PdCl2(dppf).CH2Cl2 in a reaction tube under nitrogen were added 4 ml dioxane, 0.43 ml (3 mmol) triethylamine, 0.23 ml (1.5 mmol) pinacolborane and 262 mg (1.06 mmol) 1-iodo-3,4-methylenedioxybenzene. The reaction solution was warmed to 80 C. with stirring in an oil bath for 22 h. An aliquot (0.3 ml) was removed from the reaction and extracted into ethyl acetate and washed several times with water and analysed by gc (fid detector, SGE HT5 capillary column). All the 1-iodo-3,4-methylenedioxybenzene had reacted to form the boronic acid ester together with some 1,3-benzodioxole. After addition of 8 ml methanol (which destroys the excess pinacolborane and thereby prevents the formation of symmetrical biaryl), 1.07 g Cs2CO3 and 261 mg (1.06 mmol) 4-iodobenzamide, the solution was warmed to 40 C. for 17 h. An aliquot (0.5 ml) was removed from the reaction solution and extracted into ethyl acetate and washed several times with water and analysed by gc (fid detector, SGE HT5 capillary column). The required biaryl (identified by gc/ms) gave rise to the strongest peak in the gc trace.

The chemical industry reduces the impact on the environment during synthesis 5-Iodobenzo[d][1,3]dioxole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Commonwealth Scientific and Industrial Research Organisation; US6680401; (2004); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 4949-69-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4949-69-3 name is 4-Iodo-3-methylaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 4-iodo-3-methylaniline (200 mg, 0.86 mmol) in benzene (5 mL) in a sealable tube was added 1- isocyanato-3- (trifluoromethyl)benzene (0.133 mL, 0.94 mL; “E” is an electrophilic group disussed in scheme 3, and here is an isocyanate) . The tube was sealed and heated at 90 C for 4 h. The mixture was allowed to cool to room temperature before filtering. The off white solid was washed with additional benzene (10 mL) and used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Iodo-3-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; WO2006/44823; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, 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. Computed Properties of C8H8INO2

(E)-3-(Naphthalen-2-yl)but-2-enoic acid (1.00 g, 4.71 mmol) was suspended in dry dichloromethane (15 mL) in a flame dried flask under an argon atmosphere and cooled to 0 C. Oxalyl chloride (0.848 g, 0.447 mL, 9.42 mmol) and a catalytic amount of DMF (2 drops) was added to the suspension and allowed to warm to room temperature. The solution was stirred at room temperature for 5 h after which all volatiles were removed under reduced pressure. The crude product was redissolved in dry dichloromethane (15 mL) and solvent removed under reduced pressure three times before drying under high vac. The crude product was redissolved in dry THF (20 mL) in a flame-dried flask under an argon atmosphere. To this was added 5-iodo-2-aminobenzoate (1.86 g, 7.07 mmol), pyridine (1.12 g, 1.14 mL, 14.1 mmol) and a catalytic amount of DMAP (0.01 g, 0.082 mmol). After stirring at 60 C for 16 h, the reaction was allowed to cool to room temperature, poured onto 1 N HCl and extracted into diethyl ether. The combined organic layers were dried over anhydrous magnesium sulphate and concentrated under vacuum to give the crude product.Purification by flash chromatography (8% methanolin dichloromethane) afforded the analytically pure product. (Yield:1.60 g, 3.39 mmol, 72%).1H NMR (CDCl3, 500 MHz, 20 C): delta =11.18(s, 1H, NH), 8.70 (d, J = 9.1 Hz, 1H, ArH), 8.36 (d, J = 2.2 Hz, 1H, ArH),7.98 (d, J = 1.3 Hz, 1H, NpH), 7.89 (m, 3H, ArH NpH), 7.83 (d,J = 2.2 Hz, 1H, NpH), 7.64 (dd, J = 8.5, 1.9 Hz, 1H, NpH), 7.53 (m, 2H,NpH), 6.37 (q, J = 0.9 Hz, 1H, COCH), 3.95 (s, 3H, COOCH3), 2.77 (d,J = 1.0 Hz, 3H, CCH3). 13C NMR (CDCl3, 125 MHz, 20 C): delta =167.6,165.3,154.0,143.1,141.7,139.6,139.3,133.4,133.1,128.5,128.2,127.6,126.6, 126.5, 125.8, 124.0, 122.2, 120.8, 116.5, 84.7, 52.6, 18.0. ESMScalcd for C22H18INNaO3 [M+Na]+: 494.0224, found 494.0221. HPLC(method A): Rt = 14.14 min.

The synthetic route of Methyl 2-amino-5-iodobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Waghorn, Philip A.; Jackson, Mark R.; Gouverneur, Veronique; Vallis, Katherine A.; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 117 – 129;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com