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With octasulfur; ammonia; In 2-methoxy-ethanol; at 160.0℃; for 18.0h;
E. 6-Bromobenzo[d]isothiazole. To a solution of 4-bromo-2-fluorobenzaldehyde (2.0 g, 9.85 mmol) in 2-methoxyethanol (10 mL) was added sulfur (316 mg, 9.85 mmol), and saturated aqueous ammonium hydroxide (10 mL). The materials were heated to 160 C. with stirring in a sealed reaction tube for 18 hours. The crude reaction was diluted with water and extracted three times with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, filtered, and the volatiles evaporated. The residue was purified using chromatography on a normal phase silica gel column with 0 to 5% ethyl acetate in hexanes. Fractions containing clean product were combined and the solvent evaporated. The material was dried under vacuum at room temperature to give the title compound (211 mg, 10%). MS (ESI) m/z (214 and 216) [M+1]+.
tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; N,N-dimethyl-formamide; at 95.0℃; for 2.0h;
D. Benzo[d]isothiazole-6-carbonitrile. To a solution of <strong>[877265-23-1]6-bromobenzo[d]isothiazole</strong> (205 mg, 0.96 mmol) in DMF (5 mL) was added dioxane (1 mL), tetrakis(triphenylphosphine)palladium(0) (167 mg, 0.144 mmol), and zinc cyanide (113 mg, 0.958 mmol). The reaction was heated to 95 C. with stirring for 2 hours, cooled, and the dioxane evaporated. The resulting solution was diluted with water and brine then extracted four times with dichloromethane. The organic solution was dried over anhydrous sodium sulfate, filtered, and volatiles evaporated. The resulting material was purified using chromatography on a normal phase silica gel column with 0 to 10% ethyl acetate in hexanes. Fractions containing clean product were combined and the solvent evaporated. The material was dried under vacuum at room temperature to give the title compound (118 mg, 77%).
With potassium acetate; tricyclohexylphosphine;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; at 110.0℃; for 0.5h;Sealed tube; Microwave irradiation;
6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]isothiazole. To a mixture of <strong>[877265-23-1]6-bromobenzo[d]isothiazole</strong> (0.86 g, 4.0 mmol)(prepared as described in WO 2008/036308), potassium acetate (0.38 mL, 6.0 mmol), bis(pinacolato)diboron (1.3 g, 5.2 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.18 g, 0.20 mmol), and tricyclohexylphosphine (0.12 g, 0.44 mmol) was added dioxane (5 mL). The resulting mixture was sealed and heated at 1 10C for 30 minutes under microwave irradiation. The mixture was cooled and passed through a short path of Celite, washing with DCM (3 x 10 mL). The combined organic phases were concentrated to give a residue that was purified by chromatography on silica gel (hexanes - 50 % EtOAc in hexanes) and triturat on with hexanes provided the product as a white powder (0.59 g, 56 %). LCMS (API-ES) m/z (%): 230.2 (100 %, M+H+); 1H NMR (400 MHz, CDCl3) delta ppm 8.95 (s, 1 H) 8.58 (s, 1 H) 7.91 - 8.02 (m, 2 H) 1.41 (s, 12 H).
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