Tag: M.W=300-400

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. 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, A new synthetic method of this compound is introduced below., COA of Formula: C7H4BrIO2

5-Bromo-2-iodobenzoic acid (409 mg, 1.25 mmol), A-(3-dimethylaminopropyl)-/V’- ethylcarbodiimide hydrochloride (288 mg, 1.5 mmol), 1 -hydroxybenzotri azole (135 mg, 1.0 mmol), AOY-diisopropyl ethyl amine (523 pL, 3.0 mmol), and benzyl amine (109 pL, 1.0 mmol) were dissolved in anhydrous DMF (5 mL) and stirred at room temperature for 16 hr. The reaction mixture was diluted with an excess of EtOAc and washed five times with water and brine. The organic layer was dried over Na2S04, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc : DCM = 0 : 100 to 30 : 70) to give N- benzyl-5-bromo-2-iodobenzamide (361 mg, 87 %) as a white solid.

The synthetic route of 21740-00-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; DE CLERCQ, Dries; JANG, Jaebong; JANNE, Pasi; TO, Ciric; ECK, Michael; PARK, Eunyoung; HEPPNER, David; (0 pag.)WO2019/164953; (2019); A1;,
Iodide – Wikipedia,
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Some common heterocyclic compound, 289039-20-9, name is 5-Bromo-2-iodobenzamide, molecular formula is C7H5BrINO, 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. Product Details of 289039-20-9

STEP 2. Preparation of (4-Bromo-1,1′-biphenyl-2-yl)methylamine Palladium(0) tetrakis(triphenylphosphine) (2.6 g, 2.2 mmol) was added to a stirred solution of 5-bromo-2-iodobenzamide (14.1 g, 43.3 mmol), phenyl boronic acid (5.3 g, 43.3 mmol), and potassium carbonate (24.4 g, 176.8 mmol) in degassed dimethylformamide (100 mL). The reaction was refluxed overnight under N2(g). The brown solution was cooled and filtered through Celite. The solution was diluted in ethyl acetate, washed with water, 1 N HCl, saturated sodium bicarbonate, and saturated NaCl, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to a tar. Flash chromatography (silica, 50% ethyl acetate/hexane) gave a tan solid (2.4 g). The biphenyl amide was dissolved in tetrahydrofuran (20 mL), and BH3-THF (1N, 20 mL, 20 mmol) was added slowly. The reaction was refluxed overnight under N2. The reaction was cooled to 0 C. and quenched with ethyl acetate resulting in gas evolution. After gas evolution ceased, the organics were washed with water, saturated sodium bicarbonate, saturated NaCl, dried (sodium sulfate), filtered, and concentrated yielding (4-bromo-1,1′-biphenyl-2-yl)methylamine as a gray semi-solid (2.4 g). ESI MS m/z 262.0/264.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 289039-20-9, its application will become more common.

Reference:
Patent; John, Varghese; Hom, Roy; Sealy, Jennifer; Tucker, John; US2006/14737; (2006); A1;,
Iodide – Wikipedia,
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Related Products of 1320266-94-1,Some common heterocyclic compound, 1320266-94-1, name is 1-Iodo-3-isopropylimidazo[1,5-a]pyrazin-8-amine, molecular formula is C9H11IN4, 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.

1 -(4-(8-amino-3 -isopropylimidazo[ 1 ,5-a]pyrazin- 1 -yl)phenyl)-3 -(3 – (trifluoromethyl)phenyl)urea (KIRA2). A mixture of compound 1 (22.1 mg, 0.073 mmol), compound 2 (35.5 mg, 0.087 mmol), tetrakis(triphenylphosphine)palladium (2.6 mg, 2.1 muetaiotaomicron) and sodium carbonate (17.0 mg, 0.161 mmol) was dissolved in a 3: 1 mixture of DME/water (280 uL). The mixture was heated overnight at 85 C. The crude mixture was then allowed to cooled to room temperature, diluted in a mixture of acetonitrile/water and purified by reverse phase chromatography (HPLC) to obtain 11.5 mg of KIRA2 (35% yield). TLC (CH2C12:MeOH, 95:5 v/v): Rf = 0.5; 1H NMR (300 MHz, MeOD): delta 7.95 (s, 1H), 7.68-7.64 (m, 1H), 7.65-7.63 (m, 2H), 7.60-7.56 (m, 2H), 7.55-7.48 (m, 2H), 7.34-7.31 (m, 1H), 7.02-7.00 (dd, J = 6.0 Hz, J = 3.0 Hz, 1H), 3.49-3.43 (m, 1H), 1.44 (d, J = 6.0 Hz, 6H); ESI-MS (m/z): [M]+ calcd. for C23H21F3N60, 454.17; [M+l]+ found, 455.5. HPLC Purification Conditions: C18 column (250 x 21 mm), CH3CN/H2 O-0.1% CF3C02H = 1 :99 to 100:0 over 78 min; 8 mL/min; 220 nm and 254 nm detection for 78 min. The purity of GP 1 17 was determined to be >98% by analytical HPLC in two different solvent systems.

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-3-isopropylimidazo[1,5-a]pyrazin-8-amine, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; MALY, Dustin J.; BACKES, Bradley, J.; OAKES, Scott, A.; PAPA, Feroz, R.; GHOSH, Rajarshi; WANG, Likun; (220 pag.)WO2016/4254; (2016); A1;,
Iodide – Wikipedia,
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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. 6326-42-7, name is Methyl 2-iodo-4-nitrobenzoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H6INO4

To a mixture of ammonium chloride (122 g) and iron (38.2 g) in ethanol (1000 mL) and water (100 mL) was added Example 2.140.2 (70 g,) at room temperature. The mixture was stirred at 80 C for 4 hours and filtered to remove insoluble material. The filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (1000 mL) and washed with water (500 mL). The aqueous phase was extracted with ethyl acetate (1000 mL x 2). The combined organic phase was washed with brine, dried over MgSO4, filtered and concentrated to give the title compound. MS (LC-MS) m/e 278.0 (M+H)+.

According to the analysis of related databases, 6326-42-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE INC.; BENATUIL, Lorenzo; BRUNCKO, Milan; JUDD, Andrew, S.; LI, Yingchun; MCCLUSKEY, Andrew; PHILLIPS, Andrew, C.; PHILLIPS, Darren, C.; SEAGAL, Jane; SOUERS, Andrew, J.; (808 pag.)WO2017/214462; (2017); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 5-bromo-2-iodobenzoate

500ml three-necked round bottom flask was charged with methyl 5-bromo-2-iodo benzoate (130g, 0.381mol), as 9-phenanthrene boronic acid(84.7g, 0.381mol), 2% of tetrakis triphenylphosphine palladium (8.82g, 0.008mol), 2M potassium carbonate (100ml), tetrahydrofuran (200ml) was added. 16 hours with stirring and reflux under reduced pressure and then extracted with ethyl acetate concentrate was purified by silica gel column (ethyl acetate: heptane = 1: 5) to give the [intermediate 1-a] (120g, yield = 80.4%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 181765-86-6.

Reference:
Patent; SFC CO., LTD.; JU MAN, SONG; HEE DAE, KIM; YUR IM, LEE; SANG WOO, PARK; PARK, SEOK BAE, PARK; KYUNG SEOK, JEONG; SOON WOOK, CHA; (36 pag.)KR2015/113642; (2015); A;,
Iodide – Wikipedia,
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51839-15-7, name is Dimethyl 5-iodoisophthalate, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C10H9IO4

A mixture of dimethyl 5-iodo-benzerte-1,3-dicarboxylate (9) (320 mg, 1.00 mmol), bis(pinacolato)diborane (10) (279 mg, 1.10 mmol), potassium acetate (294 mg, 3.00 mmol), PdCl2(dppf)* (24 mg, 0.03 mmol) and dried DMF (6 mL) was stirred at 80C for 2 h. The reaction mixture was cooled to the room temperature. Then, dimethyl 5-iodo-benzene-1,3-dicarboxylate (9) (640 mg, 2.00 mmol), PdCl2(dppf) (24 mg, 0.03) and CsF (456 mg, 3.0 mmol; dissolved in 2.5 mL of water) were added. The mixture was stirred at 80C overnight and afterwards extracted for four times with diethylether (4 x 25 mL). The organic layer was dried with MgSO4 and the solvent was removed in vacuum. The crude product was purified by column chromatography (silica gel, ethylacetate/hexane, 3:7 v/v). Yield 82 %. M.p. 214-215 C. 1H-NMR (400 MHz, CDCl3): delta= 4.00 (s, 12H), 8.51 (d, 4H, J = 1.5 Hz), 8.72 (d, 2H, J = 1.5 Hz). 13C-NMR (100 MHz, CDCl3): delta= 52.5, 130.2, 131.5, 132.3, 139.9, 165.9. Rf= 0.50 (silica gel, othylacetate/hexane, 3:7 v/v). MS-EI, m/z (%): 386 (75) [M+], 355 (100), 327 (15), 194 (10). *[1,1′-bis(diphenylphoshino)ferrocene]dichloropalladium(II)].

The synthetic route of 51839-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Technische Universitaet Carolo-Wilhelmina zu Braunschweig; EP1972338; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

628-21-7, name is 1,4-Diiodobutane, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C4H8I2

Example 3 (n=4); (a) 1, 1′-[(Butane-1,4-diyl)dioxy]bis[(11S,11aS)-10-(tert- butyloxycarbonyl)-8-methoxy-ll- (tetrahydro-pyran-2-yloxy)- 1, 2,3, 10, 11, 11a-hexahydro-5H-pyrrolo[2,-c][1,4]benzodiazepine-5-one](8b); 1,4-Diiodobutane (69.1 mg, was added to the mixture of monomer 7 (0.2 g, 0.44 mmol, 1.0 equiv) and potassium carbonate (0.98 mmol, 2.2 equiv) in dry DMF (30 mL), and the resulting mixture was heated to 90C under a nitrogen atmosphere for 5 h. Removal of excess solvent under reduced pressure afforded a crude solid, which was subjected to flash column chromatography (SiO2, 50% EtOAc- hexane) to afford the dimerized compound 8b (134 mg, 0.14 mmol, 63% yield, mixture of diastereomers from THP protecting group as a solid: [a] 20D = +36 (c = 0. 19, CHCl3) ; 1H NMR (CDC, 400 MHz): 5 1.35 (s, 36H, Boc), 1.45-1. 67 (m, 16H, THP), 1.68-1. 86 (m, 8H, THP), 1.90-2. 21 (m, 24H, 1-H, 2-H, 13-H), 3.44-3. 78 (m, 16H, 3-H, lla-H, THP), 3.84-4. 02 (m, 16H, 7-OMe, THP), 4. 04-4. 25 (m, 8H, 12- H), 5.02-5. 10 (m, 2H, THP), 5.11-5. 20 (m, 2H, THP), 5.69-5. 77 (d, 2H, 11-H), 5.79-5. 89 (d, 2H, 11-H), 6.51 (s, 2H, 9-H), 6.88 (s, 2H, 9-H), 7.19 (s, 2H, 6-H), 7.28 (s, 2H, 6-H) ; 13C NMR (CDCl3, 400 MHz): No. 19.8, 20.5, 23.1, 23.2, 25.3, 25.9, 28.1, 28. 2,28. 9, 29.1, 30.9, 31.2, 46.2, 55.9, 56.2, 60.1, 63.3, 63.6, 68.6, 80.9, 88.2, 91.2, 96.2, 100.2, 111.1, 111.4, 113.4, 114.1, 118.5, 126.4, 129.8, 143.1, 147.9, 148.2, 151. 5, 151. 8,155. 8,167. 4,167. 6; IR (neat): 2945,1704, 1644, 1604,1513, 1449,1392, 1327,1217, 1163, 1022cm~1 ; MS (FAB) m/z (relative intensity) 973 ([M + Na] +, 11), 951 (M +, 100), 749 (36).

The synthetic route of 628-21-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SPIROGEN LIMITED; WO2005/85259; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 811842-30-5, name is 2-Bromo-1-fluoro-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. Recommanded Product: 2-Bromo-1-fluoro-4-iodobenzene

Add 9H-purin-2-amine (135 mg, 1 mmol), 2-bromo-1-fluoro-4-iodobenzene (600 mg, 2 mmol), potassium carbonate (415 mg, 3 mmol) and proline(23 mg, 0.2 mmol) to the eggplant type flask, dimethyl sulfoxide was added, and the reaction solution was deoxidized. Copper iodide (19 mg, 0.1 mmol) was added and the reaction solution was deoxygenated. Heat to 90 C and stir for 16 hours. After the reaction was completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixture was filtered over Celite.The target compound (QC87-1) 40 mg was obtained, ESI-MS calc. C11H779BrFN5[M+H]+= 307.99; experimentally measured: 307.39;the target compound (QC87-2) 40 mg was obtained.

The synthetic route of 2-Bromo-1-fluoro-4-iodobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Zhiqiang; Yan Ziqin; Li Jia; Zhou Yubo; Su Mingbo; Chen Zheng; (138 pag.)CN109810110; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 181765-86-6,Some common heterocyclic compound, 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, molecular formula is C8H6BrIO2, 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.

2,9 g (14,9 mmol) of (1 , 1′-biphenyl)-2-yl-boronic acid, 4,6 g (13,6 mmol) of methyl 5-bromo-2-iodobenzoate, 314 mg (0,3 mmol, 0,02 eq.) of Pd(P(Ph3))4, 5,6 g (40,7mmol, 3 eq.) of Na2C03 are dissolved in 7 mL of water and 30 mL of toluene. The reaction mixture is stirred at 85C and agitated under an argon atmosphere for 12 hours and after cooling to room temperature, the mixture is filtered through Celite. The filtrate is evaporated in vacuo, and the residue is purified by (0273) chromatography (mixture heptane/AcOEt). The product is isolated in the form of an off-white solid (4,5 g 91 % of theory).

The synthetic route of 181765-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; MONTENEGRO, Elvira; MUJICA-FERNAUD, Teresa; MAIER-FLAIG, Florian; VOGES, Frank; COMELY, Alexander; MORENO FLORES, Rosa; (201 pag.)WO2019/115577; (2019); 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. 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 5-bromo-2-iodobenzoate

(a) 5-Bromo-2-(4-nitrobenzoyl)benzoic acid methyl ester; /-PrMgCI LiCI in THF (1.25M.17.6 ml_, 22 mmol) was added to 5-bromo-2-iodo- benzoic acid methyl ester (6.82 g, 20 mmol) in THF (40 ml_) at -40 0C over 5 min. The mixture was stirred at -30 0C for 1 h, cooled to -78 0C and added to 4-nitro- benzoyl chloride (7.42 g, 40 mmol) in THF (30 mL) at -78 0C. The temperature was allowed to reach rt and NaHCO3 (aq, sat) was added. Extractive workup (EtOAc, NaHCO3 (aq, sat), H2O, brine), drying (K2CO3 and Na2SO4), concentration and crystallization from EtOAc gave the sub-title compound. Yield: 5.48 g (75%).

The synthetic route of 181765-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOLIPOX AB; NILSSON, Peter; PELCMAN, Benjamin; KATKEVICS, Martins; WO2010/103279; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com