Stage #1: at 20℃; for 0.333333 h; Stage #2: at 50℃;
Example 30; 7-Bromo-benzothiazoleSodium nitrite (0.229 g, 3.3 mmol) was added to a solution of 7-bromo-benzothiazol-6-ylamine (0.380 g, 1.66 mmol, described in WO 97/31636) in sulfuric acid (10 mL) and the resulting mixture was stirred at room temperature for 20 min. Hypophosphorous acid (10 mL) was added and the mixture was heated at 50° C. overnight. The pH was adjusted to 9-10 by addition of sodium carbonate, and the crude product was removed by filtration and washed with water. Purification by prep-HPLC gave 0.265 g (75percent yield) of the title compound as a white solid: LC-MS (EI) m/z 213 (M++1).
42%
Stage #1: at 20℃; for 1 h; Stage #2: at 0℃; for 1 h;
To 7-bromobenzo[djthiazol-6-amine (2-18, 1 g, 4.4 mmol) in H2S04 (5 ml) was added NaNO2 (605 mg, 8.8 mmol) at 0 °C and the resulting reaction mixture was stirred for 20 mm. H3P02 (5 ml) was then added at 0 °C, and the mixture was stirred for 1 h. Upon reaction completion, the mixture was washed with saturated NaHCO3, extracted with ethyl acetate (50 mL x 3), and the combined organic phases were concentrated under reduced pressure to provide intermediate 2-19 (yellow solid, 400 mg, 42percent yield). LCMS (m/z): 214 [M + HI .
30%
Stage #1: at 0 - 5℃; for 0.25 h; Stage #2: at 20℃;
To a solution of bromobenzo[d]thiazol-6-amine (30 mg, 0.13mmol) was added 50percent H2SO4 (38 mg, 0.39mmol), and then NaNO2 (18 mg, 0.26mmol) was added to the mixture at 0-5 0C. The reaction mixture was stirred about 15 min at 0-5 0C, 50percent H3PO2 (17 mg, 0.26mmol) was added. The mixture was stirred at room temperature overnight, quenched with aq.NaHCO3 solution, extracted with ethyl acetate. The combined organic layer was concentrated under vacuum to give a residue which was purified with chromatography (ethyl acetate/petroleum ether=0.06) to give 7-bromobenzo[d]thiazole (10 mg, 30percent).
Example 30; 7-Bromo-benzothiazoleSodium nitrite (0.229 g, 3.3 mmol) was added to a solution of <strong>[769-20-0]7-bromo-benzothiazol-6-ylamine</strong> (0.380 g, 1.66 mmol, described in WO 97/31636) in sulfuric acid (10 mL) and the resulting mixture was stirred at room temperature for 20 min. Hypophosphorous acid (10 mL) was added and the mixture was heated at 50 C. overnight. The pH was adjusted to 9-10 by addition of sodium carbonate, and the crude product was removed by filtration and washed with water. Purification by prep-HPLC gave 0.265 g (75% yield) of the title compound as a white solid: LC-MS (EI) m/z 213 (M++1).
42%
To 7-bromobenzo[djthiazol-6-amine (2-18, 1 g, 4.4 mmol) in H2S04 (5 ml) was added NaNO2 (605 mg, 8.8 mmol) at 0 C and the resulting reaction mixture was stirred for 20 mm. H3P02 (5 ml) was then added at 0 C, and the mixture was stirred for 1 h. Upon reaction completion, the mixture was washed with saturated NaHCO3, extracted with ethyl acetate (50 mL x 3), and the combined organic phases were concentrated under reduced pressure to provide intermediate 2-19 (yellow solid, 400 mg, 42% yield). LCMS (m/z): 214 [M + HI .
30%
To a solution of bromobenzo[d]thiazol-6-amine (30 mg, 0.13mmol) was added 50% H2SO4 (38 mg, 0.39mmol), and then NaNO2 (18 mg, 0.26mmol) was added to the mixture at 0-5 0C. The reaction mixture was stirred about 15 min at 0-5 0C, 50% H3PO2 (17 mg, 0.26mmol) was added. The mixture was stirred at room temperature overnight, quenched with aq.NaHCO3 solution, extracted with ethyl acetate. The combined organic layer was concentrated under vacuum to give a residue which was purified with chromatography (ethyl acetate/petroleum ether=0.06) to give 7-bromobenzo[d]thiazole (10 mg, 30%).
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