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Structure of 17249-80-8 * Storage: {[proInfo.prStorage]}
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Bulletin of the Chemical Society of Japan, 2012, vol. 85, # 3, p. 369 - 371
20
[ 17249-80-8 ]
[ 124-38-9 ]
[ 59337-89-2 ]
[ 59614-95-8 ]
Reference：
[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3471 - 3488
21
[ 17249-80-8 ]
[ 1692-15-5 ]
[ 21308-82-7 ]
Reference：
[1] Journal of the American Chemical Society, 2007, vol. 129, # 11, p. 3358 - 3366
22
[ 17249-80-8 ]
[ 88303-25-7 ]
[ 110851-66-6 ]
Reference：
[1] Angewandte Chemie - International Edition, 2002, vol. 41, # 4, p. 609 - 612
[2] Journal of the American Chemical Society, 2002, vol. 124, # 46, p. 13856 - 13863
[3] Patent: US2003/220498, 2003, A1, . Location in patent: Page/Page column 6
23
[ 17249-80-8 ]
[ 77893-68-6 ]
Yield
Reaction Conditions
Operation in experiment
100%
With N-Bromosuccinimide; acetic acid In chloroform for 1.5 h; Reflux
Compound 28-1 (0457) To a solution of 3-chlorothiophene (6.52 g, 55 mmol) in CHCl3 (30 mL) and AcOH (30 mL) was added NBS (9.80 g, 55 mmol). The mixture was heated at relux for 1.5 h, then cooled to room temperature. Water (70 mL) was added and the mixture was extracted with CHCl3 (30 mL×2). The combined organic layers were washed with sat. NaHCO3 (40 mL) and brine (30 mL), dried over anhydrous Na2SO4, filtered, concentrated to afford 28-1 as a brown oil (10.02 g, quantitive yield) which used for the next step directly.
93%
With N-Bromosuccinimide; acetic acid In chloroform at 20℃; for 18 h; Inert atmosphere; Cooling with ice
Under a nitrogen atmosphere, 3-chloro-thiophene 300ml three-necked flask (Sigma - Aldrich) 1.18 g (0.010 mol), chloroform 10ml and acetic acid was added 10ml.Under ice-cooling N- bromosuccinimide (manufactured by Wako Pure Chemical Industries) 1.96 g of (0.011 mol) was added dropwise and stirred for 18 hours at room temperature.Ice-cold sewage added to the reaction solution, followed by extraction with chloroform, the organic phase was washed with brine, dried over anhydrous sodium sulfate, to give a colorless liquid 1.84g of 2-bromo-3-chloro-thiophene (yield: 93percent).
53%
With bromine In tetrachloromethane at 0 - 60℃; for 18 h;
Example 1080 Neat bromine (0.8 mL, 24 mmol, 0.9 eq) was added dropwise over ~20 min to a stirred solution of Compound 1080A (2.00 g, 0.026 mmol) in carbon tetrachloride (4 mL) at 0 0C. Upon completion of the addition, the reaction mixture was heated at 60 deg:C for 18 h. The reaction mixture was diluted with Et&2O (50 mL), and was washed sequentially with saturated aq sodium bicarbonate (50 mL) and brine (-50 ml_). The organic phase was dried over anhydrous MgSO4, filtered, and concentrated. The desired product 1080B was purified by sgc (100percent hexanes, isocratic) to give Compound 1080B as a clear, colorless liquid (1.78 g, 53percent)
97%
With N-Bromosuccinimide; perchloric acid In <i>N</i>-methyl-acetamide
A solution of N-bromosuccinimide (221.7 g) in dimethylformamide (550 ml) was added dropwise over 75 min to a stirred solution of 3-chlorothiophene (143.4 g) and perchloric acid (70percent, 5.8 ml) cooled in an ice-water bath at 15° C. The reaction temperature gradually rose to 40° C. over 30 min and then was cooled to 11° C. Cooling was removed and the reaction was stirred for a further 2 h. The reaction was poured into water and exacted with methyltertbutyl ether. The organic extract was sequentially washed with water, aq. sodium hydrogen sulphite solution and water, dried (Na2SO4) and evaporated to dryness. The residual oil (246 g) was distilled under vacuum in an oil bath at 80-90° C. to give 2-bromo3-chloro-thiophene as an oil (202 g (97percent); b pt 42° C. (1 mm Hg).
Reference：
[1] Patent: US9138427, 2015, B2, . Location in patent: Page/Page column 304
[2] Patent: JP2015/227295, 2015, A, . Location in patent: Paragraph 0047
[3] Synthetic Communications, 1994, vol. 24, # 1, p. 95 - 101
[4] Journal of Medicinal Chemistry, 1981, vol. 24, # 8, p. 959 - 964
[5] Patent: WO2007/84451, 2007, A1, . Location in patent: Page/Page column 154
[6] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 3, p. 617 - 620
[7] Patent: US6288085, 2001, B1,
[8] Patent: WO2013/119895, 2013, A1, . Location in patent: Page/Page column 72
[9] Patent: WO2014/98831, 2014, A1, . Location in patent: Page/Page column 64
[10] Patent: WO2018/160878, 2018, A1, . Location in patent: Page/Page column 309
24
[ 17249-80-8 ]
[ 124-38-9 ]
[ 59337-89-2 ]
[ 59614-95-8 ]
Reference：
[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3471 - 3488
With N-Bromosuccinimide; acetic acid; In chloroform; for 1.5h;Reflux;
Compound 28-1 (0457) To a solution of 3-chlorothiophene (6.52 g, 55 mmol) in CHCl3 (30 mL) and AcOH (30 mL) was added NBS (9.80 g, 55 mmol). The mixture was heated at relux for 1.5 h, then cooled to room temperature. Water (70 mL) was added and the mixture was extracted with CHCl3 (30 mL×2). The combined organic layers were washed with sat. NaHCO3 (40 mL) and brine (30 mL), dried over anhydrous Na2SO4, filtered, concentrated to afford 28-1 as a brown oil (10.02 g, quantitive yield) which used for the next step directly.
96.07%
With N-Bromosuccinimide; acetic acid; In chloroform; at 20 - 100℃; for 2.5h;
3-chlorothiophene BB-4-1 (50.00 g, 421.66 mmol, 1.00 eq) was solved in CHCl3 (200.00 mL) and acetic acid(200.00 mL), and the mixture was added N-bromosuccinimide (75.05 g, 421.66 mmol, 1.00 eq). The reaction mixturewas stirred for 30min at 20C, warmed to 100C and refluxed for 2h, and the mixture turned to brown clarified liquid fromyellow muddy. Then the mixture was poured into water (200 mL) and extracted with DCM (150 mL 3 3). The DCMphases were combined, washed with sat.aq Na2CO3 (150 mL) and then with sat.aq NaCl (100 mL), dried over anhydrousNa2SO4, the drier was filtered out and the filtrate was concentrated under reduced pressure to remove solvents andgive crude product, compound BB-4-2 (80.00 g, 405.10 mmol, 96.07% yield) as yellow oil which could be used for nextstep without further purification. 1H NMR (400MHz, CDCl3) delta: 7.28 (d, J=2.0 Hz, 1H), 6.89 (d, J=2.0 Hz, 1H).
93%
With N-Bromosuccinimide; acetic acid; In chloroform; at 20℃; for 18h;Inert atmosphere; Cooling with ice;
Under a nitrogen atmosphere, 3-chloro-thiophene 300ml three-necked flask (Sigma - Aldrich) 1.18 g (0.010 mol), chloroform 10ml and acetic acid was added 10ml.Under ice-cooling N- bromosuccinimide (manufactured by Wako Pure Chemical Industries) 1.96 g of (0.011 mol) was added dropwise and stirred for 18 hours at room temperature.Ice-cold sewage added to the reaction solution, followed by extraction with chloroform, the organic phase was washed with brine, dried over anhydrous sodium sulfate, to give a colorless liquid 1.84g of 2-bromo-3-chloro-thiophene (yield: 93%).
53%
With bromine; In tetrachloromethane; at 0 - 60℃; for 18h;
Example 1080 Neat bromine (0.8 mL, 24 mmol, 0.9 eq) was added dropwise over ~20 min to a stirred solution of Compound 1080A (2.00 g, 0.026 mmol) in carbon tetrachloride (4 mL) at 0 0C. Upon completion of the addition, the reaction mixture was heated at 60 °:C for 18 h. The reaction mixture was diluted with Et2O (50 mL), and was washed sequentially with saturated aq sodium bicarbonate (50 mL) and brine (-50 ml_). The organic phase was dried over anhydrous MgSO4, filtered, and concentrated. The desired product 1080B was purified by sgc (100% hexanes, isocratic) to give Compound 1080B as a clear, colorless liquid (1.78 g, 53%)
202 g (97%)
With N-Bromosuccinimide; perchloric acid; In N-methyl-acetamide;
A solution of N-bromosuccinimide (221.7 g) in dimethylformamide (550 ml) was added dropwise over 75 min to a stirred solution of 3-chlorothiophene (143.4 g) and perchloric acid (70%, 5.8 ml) cooled in an ice-water bath at 15 C. The reaction temperature gradually rose to 40 C. over 30 min and then was cooled to 11 C. Cooling was removed and the reaction was stirred for a further 2 h. The reaction was poured into water and exacted with methyltertbutyl ether. The organic extract was sequentially washed with water, aq. sodium hydrogen sulphite solution and water, dried (Na2SO4) and evaporated to dryness. The residual oil (246 g) was distilled under vacuum in an oil bath at 80-90 C. to give 2-bromo3-chloro-thiophene as an oil (202 g (97%); b pt 42 C. (1 mm Hg).
With bromine; In 1,4-dioxane; at 0 - 60℃;
Preparation 61 2-bromo-3 -chlorothiophene To a solution of 3 -chlorothiophene (15 g, 126 mmol) in dioxane (42.2 ml) at 0 C was added bromine (7.01 ml, 136 mmol) dropwise over 30 min. When the addition was complete, the reaction mixture was brought to 60 C and stirred overnight. The mixture was then allowed to come to rt at which time it was washed with saturated aqueous sodium bicarbonate (3 x 15 mL). The remaining organic layer was dried over MgS04, filtered and concentrated in vacuo. Distillation of the resulting oil (lit. BP: 194C/760mm Hg, 47C/0.1mm Hg) gave 2-bromo-3 -chlorothiophene (18.2 g, 92 mmol, 72.9 % yield) as a clear, colorless oil containing some impurities. This was used as-is; NMR (500MHz, CHLOROFORM-d) delta 7.33 - 7.24 (m, 2H), 6.90 (d, J=5.8 Hz, 1H) with impurities showing between 4.0 and 3.5 ppm.
With bromine; In tetrachloromethane; at 0 - 20℃; for 12h;
To a stirred solution of compound 138 (5 g, 42.37 mmol) in CCl4 (30 mL) at 0C, Br2 (6.4 g, 40.25 mmol) was added drop wise. The resulting reaction mixture was stirred room temperature for 12 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was cooled to 0C; quenched by adding aq. Sodium thiosulphate and 50% NaOH solution and extracted with DCM. The combined organic layers were collected, dried over anhydrous sodium sulphate and concentrated in vacuo to afford the title compound 139 (6 g, 71.94%) as a colorless liquid and used as such for the next step without further purification TLC: hexane (Rf: 0.4); 1H NMR (DMSO-d6, 400 MHz): delta 7.75 (d, J = 5.6 Hz, 1H), 7.11 (d, J = 6.0 Hz, 1H).
With bromine; In 1,4-dioxane; at 0 - 60℃; for 18h;
Example 1071 Step 1 Neat bromine (1.4 mL, 28 mmol, 1.1 eq) was added dropwise to a stirred solution of Compound 1071A (3.0 g, 26 mmol) in dioxane (8 mL) at 0 0C. Upon completion of the addition, the reaction mixture was heated at 60 0C for 18 h. The reaction mixture was diluted with Et2O (50 mL), and was washed sequentially with saturated aq sodium bicarbonate (50 mL) and brine (~50 mL). The organic phase was dried over anhydrous MgSO4, filtered, and concentrated. The desired product, Compound 1071 B, was separated from the crude product by sgc (0-10% EtOAc-hexanes). Yield: 0.987 g, 15% yield.
With n-butyllithium; In diethyl ether; hexane; at -10 - 20℃; for 0.333333h;
To a solution of <strong>[17249-80-8]<strong>[17249-80-8]3-chlorothiophen</strong>e</strong> (1.16 ml) in ether (20 ml) at -10 C. was added n-BuLi (2.5M in hexane, 5 ml). After solution was stirred at -10 C. for 20 min, propionaldehyde (0.82 ml) in ether (20 ml) was added dropwise and let warm to room temperature slowly. The reaction was quenched with saturated ammonium chloride and extracted with CH2Cl2, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 1.37 g of product (62%).
62%
To a solution of <strong>[17249-80-8]<strong>[17249-80-8]3-chlorothiophen</strong>e</strong> (1. 16ml) in ether (20ml) at-10C was added n-BuLi (2.5M in hexane, 5ml). After solution was stirred at-10 C for 20min, propionaldehyde (0. 82ml) in ether (20ml) was added dropwise and let warm to room temperature slowly. The reaction was quenched with saturated ammonium chloride and extracted with CH2CI2, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 1.37g of product (62%).
2-Chloro-5-nitrophenyl 3-chloro-thien-2-yl ketone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
aluminium trichloride; In dichloromethane;
EXAMPLE 8 Preparation of 2-Chloro-5-nitrophenyl 3-chloro-2-thienyl ketone To a mixture of aluminum chloride (1.33 g, 0.0102 mol) and methylene chloride is added <strong>[17249-80-8]<strong>[17249-80-8]3-chlorothiophen</strong>e</strong> (1.21 g, 0.0102 mol) dropwise. The resultant mixture is stirred 30 minutes and treated with a solution of 2-chloro-5-nitrobenzoyl chloride (2.20 g, 0.0100 mol) in methylene chloride. The resultant mixture is stirred overnight at room temperature, poured into ice, acidified with concentrated hydrochloric acid and extracted twice with methylene chloride. The combined organic layers are washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to a brown oil. Trituration with ether affords the title compound as a brown solid (1.33 g, 44.0%, mp 114-116 C.) which is identified by NMR spectral analysis. In essentially the same manner, treatment of 2-chloro-5-nitrobenzoyl chloride with 2,5-dimethylthiophene affords the following compound:
5-chloro-7-[2-(pyridin-2-yl)ethyl]-2-(thien-3-yl)-benzoxazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With methanesulfonic acid; In 1,4-dioxane; toluene;
EXAMPLE 4 Preparation of 5-chloro-7-[2-(pyridin-2-yl)ethyl]-2-(thien-3-yl)-benzoxazole This compound is prepared from 2-amino-4-chloro-6-[2-(pyridin-2-yl)ethyl]phenol, and <strong>[17249-80-8]3-thienyl chloride</strong> using method A with 1,4-dioxan as solvent to give the crude amide in a 100% yield. This is treated with methanesulphonic acid in toluene at reflux, with azeotropic removal of water. Purification by flash chromatography (SiO2, EtOAc:hexanes 1:1), gave the title compound, (30%) as a white crystalline solid, m.p. 126-127 C. TLC (SiO2, EtOAc:hexanes 1:1, Rf=0.46). CI Mass Spectrum (methane), m/z=341 [M+H]+.
(3-chloro-thiophen-2-yl)-trimethylsilane[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With n-butyllithium; In tetrahydrofuran; hexane;
EXAMPLE 1A 2-Trimethylsilyl-<strong>[17249-80-8]<strong>[17249-80-8]3-chlorothiophen</strong>e</strong> STR15 To <strong>[17249-80-8]<strong>[17249-80-8]3-chlorothiophen</strong>e</strong> (5.0 g, 42.16 mmol), dissolved in 50 mL of tetrahydrofuran stirring at -72 C. (acetone/dry ice bath), was added 16.8 ml of 2.5M hexane solution of n-butyllithium over a 15 minute period. The reaction temperature was maintained below -70 C. during the addition. Soon after complete addition of the n-butyllithium a white precipitate formed.
With sulfuric acid; iodine; iodic acid; acetic acid; In hexane; water; at 40℃; for 15h;
In a 30-mL four mouth flask, <strong>[17249-80-8]<strong>[17249-80-8]3-chlorothiophen</strong>e</strong> (2 g, 16.9mmol), Iodine (1.54 g, 6.1mmol), iodic acid (0.62 g, 3.5mmol), acetic acid (4 mL), n-hexane (6 mL), water (1.5 mL), and concentrated sulfuric acid (two drops) were added, and it was made to react at 40 degrees C for 15 hours. After ending reaction, after cooling to a room temperature, a saturated sodium bicarbonate aqueous solution (10 mL) and diethylether (10 mL) were added and extracted. The sodium-hydrogen-sulfite aqueous solution (10 mL) and the saturated sodium chloride solution solution (10 mL) washed the obtained organic layer in order 10%, and it dried with magnesium sulfate. By refining the gift obtained by filtration and concentration with column chromatography (silica gel: hexane solvent), the 3-chloro-2-iodothiophene was obtained as a substantially colorless liquid at 3.7 g (90% of yield).
Step 1. 2-iodo-<strong>[17249-80-8]<strong>[17249-80-8]3-chlorothiophen</strong>e</strong>. The desired compound was prepared according to the method of Example 19, step 3, except substituting <strong>[17249-80-8]<strong>[17249-80-8]3-chlorothiophen</strong>e</strong> for 2-(4-chlorophenylmethyl)thiophene.
With n-butyllithium; diisopropylamine; In tetrahydrofuran; ethyl acetate;
Production Example 14 2-(1-Benzylpiperidin-4-yl)-1-(3-chloro-2-thienyl)ethanol After dissolving 1.3 ml of diisopropylamine in 20 ml of tetrahydrofuran, 3.5 ml of n-butyllithium (2.66 M, n-hexane solution) was added dropwise while stirring at below -30 C. After stirring for 30 minutes vhile cooling on ice, 0.86 ml of <strong>[17249-80-8]<strong>[17249-80-8]3-chlorothiophen</strong>e</strong> was added dropw.ise. The mixture was stirred for another 30 minutes, and then a solution of 1.6.8 g of 1-benzyl-4-piperidineacetaldehyde in tetrahydrofuran (5 ml) was added and stirring was continued for 1 hour. Saturated aqueous ammonium chloride solution was added to the reaction solution dnd extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (1.53 g, 59% yield). 1H-NMR (400 MHz, CDCl3); delta (ppm) 1.26-1.54 (3H, m), 1.56-1.88 (4H, m), 1.90-1.98 (2H, m), 2.83-2.91 (2H, m), 3.49 (2H, s), 5.19 (1H, dd, J=8.4, 5.6 Hz), 6.86 (1H, d, J=5.2 Hz), 7.21-7.34 (6H, m).
Step A: 2,4-Dichloro-6-(3-chloro-thiophen-2-yl)-pyrimidine To a solution of <strong>[17249-80-8]<strong>[17249-80-8]3-chlorothiophen</strong>e</strong> (384 mg, 3.0 mmol) in THF (6 mL) at -78 C. was added n-BuLi (1.6 M, 2 mL) and the resulting mixture stirred for 45 minutes. The resulting product was added to a solution of 2,4-dichloropyrimidine (430 mg, 2.9 mmol) in ether (10 mL) at -30 C. and the resulting mixture stirred for 30 minutes, then warmed up to 0 C. and stirred for another 30 minutes. DDQ (700 mg, 3 mmol) was added and the resulting mixture was stirred overnight, then filtered through Celite. The filtrate was concentrated and the residue was purified by silica gel column (EtOAc/hexanes, 1:5) to yield a white solid.
Preparation of ethyl (3-chlorothien-2-yl)(oxo)acetate: A solution of 3- chlorothiophene (5 mL, 54 mmol) in 60 mL THF was cooled in a dry ice-acetone bath before slow addition of a solution of 1.6 N n-butyllithium (35 mL, 56 mmol). After 30 minutes stirring, diethyloxalate (7.6 mL, 56 mmol) was added all at once. The mixture was slowly warmed to 0 C before being quenched with NH4Cl (aqueous) and being partitioned between water and ether. The ether was separated and washed with brine. Drying (MgS04) and removal of solvent gave 8.3 g of an oil, H NMR (300 MHz, CHLOROFORM-D) 8 ppm 1.34 (t, J=7.1 Hz, 3 H) 4.36 (q, J=7.1 Hz, 2 H) 7.02 (d, J=5.2 Hz, 1 H) 7.66 (d, J=5.2 Hz, 1 H).
With chlorosulfonic acid; In dichloromethane; at 0℃; for 2h;
3-Chlorothiophene-2-sulfonyl chloride is synthesised according to the method detailed in Bioorganic and Medicinal Chemistry Letters 1996, 6, 2651-2656:To a stirred solution of <strong>[17249-80-8]<strong>[17249-80-8]3-chlorothiophen</strong>e</strong> (10 g, 84 mmol) in dichloromethane (25 ml) cooled to 0 C. is added chlorosulfonic acid (16 ml, 252 mmol) dropwise. The reaction mixture is then stirred for 2 hours at 0 C. is and then carefully poured onto ice and extracted into dichloromethane (2×250 ml). The organics are combined and dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a mixture with the other isomer. Both isomers are separated and the title compound isolated by silica column chromatography eluting with hexane:ethyl acetate. (3.7 g, 20%), 1H NMR (500 MHz, CHLOROFORM-d) delta ppm 7.75 (1H, d, 5.3 Hz), 7.15 (1H, d, 5.3 Hz).
General procedure: To an oven dried glass vessel capable of being sealed with a Teflon cap (for microwave vials) was added XPhos-Pd-G2 (11.8mg, 15mumol), XPhos (14.3mg, 30mumol), B2(OH)4 (203mg, 2.25mmol), KOAc (441mg, 4.5mmol), and halide (only if a solid). The vessel was sealed, evacuated, and filled with an inert gas (4×). EtOH (15mL, degassed) was added via syringe followed by the addition of ethylene glycol (280mg, 250muL, 4.5mmol) and the halide (1.5mmol) in a similar manner (if applicable). The reaction was heated to the specified temperature until the starting material was consumed (as monitored by GC). The reaction was cooled, and a needle attached to a manifold under an inert atmosphere was inserted into the septum, and 3equiv of degassed K3PO4 (1M, 4.5mL, 4.5mmol) was added via syringe, and the reaction was allowed to sit for 5min. Then the second halide was added in a similar manner (as a solution in 500muL of degassed EtOH or THF if a solid). The manifold needle was removed, and the reaction was heated to the specified temperature for 24h. The reaction was cooled to rt and filtered through a very thin pad of Celite, eluting with 5×10mL of EtOAc, and then concentrated. The crude reaction was dissolved in EtOAc (10mL), transferred to a separatory funnel, and then saturated NaHCO3 (10mL) was added. The aqueous layer was extracted with EtOAc (3×5mL). The combined organics were dried (Na2SO4), filtered, and concentrated. The desired compound was purified by silica gel column chromatography, eluting with EtOAc/hexane.
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