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With triethylamine;tetrakis(triphenylphosphine) palladium(0); In acetonitrile; for 6.0h;Heating / reflux;
(3) To a solution of <strong>[864376-04-5]6-ethynylbenzothiazole</strong> (483 mg) synthesized in Example 17-(2) and 2-iodo-5-methylthiazole (740 mg) in acetonitrile (10 ml), triethylamine (15 ml) and tetrakis(triphenylphosphine) palladium (179 mg) were added under nitrogen atmosphere. This solution was heated under reflux for 6 hours under nitrogen atmosphere. After the solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=85:15 ? 50:50) to yield the title compound (601 mg) as a yellow powder (mp: 137.0-140.0C). 1H NMR (200 MHz, CDCl3) delta ppm: 2.53 (3H, d, J = 1.1 Hz), 7.53 (1H, d, J = 1.1 Hz), 7.71 (1H, dd, J = 8.5, 1.6 Hz), 8.13 (1H, dd, J = 8.5, 0.6 Hz), 8.20 (1H, dd, J = 1.6, 0.5 Hz), 9.07 (1H, s)
6-[(4-methyl-1,3-thiazol-2-yl)ethynyl]-1,3-benzothiazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
77%
With tetrakis(triphenylphosphine) palladium(0); triethylamine; In acetonitrile; for 3.5h;Reflux;
General procedure: To a solution of 22 (2.93 g, 24.4 mmol) and 2b (5.00 g, 22.2 mmol) in CH3CN (100 mL) were added Pd(PPh3)4 (1.28 g, 1.11 mmol), NEt3 (50 mL, 359 mmol). The reaction mixture was stirred at reflux temperature for 3.5 h. The reaction mixture was filtered through Celite and the filtrate was evaporated. The crude product was purified by column chromatography on silica gel eluting with 10-15% EtOAc/n-Hexane to afford 24b as a pale orange powder (3.74 g, 77%): mp 82.0-83.0 oC; 1H NMR (300 MHz, CDCl3, delta): 2.49 (d, J = 0.9 Hz, 3 H), 6.93 (d, J = 0.9 Hz, 1 H), 7.03 - 7.12 (m, 2 H), 7.52 - 7.60 (m, 2 H); MS (CI) m/z 218 [M+H]+, 100%.
With triethylamine;tetrakis(triphenylphosphine) palladium(0); In acetonitrile; for 5.0h;Heating / reflux;
Triethylamine (280 ml) and tetrakis(triphenylphosphine)palladium (6.8 g) were added to a solution of <strong>[864376-04-5]6-ethynylbenzothiazole</strong> (29.5 g) and 2-iodo-4-methylthiazole (45.9 g) in acetonitrile (600 ml) under nitrogen atmosphere. This solution was heated under reflux for 5 hours under nitrogen atmosphere. After the solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 ? 1:1) to yield the title compound (41.2 g) as a light yellow powder (mp: 116.0-117.0C). 1H NMR (200 MHz, CDCl3) delta ppm: 2.51 (3H, d, J = 0.9 Hz), 6.96 (1H, d, J = 0.9 Hz),7.71 (1H, dd, J = 8.4, 1.8 Hz), 8.12 (1H, d, J = 7.9 Hz), 8.20 (1H, d, J = 1.8 Hz), 9.07 (1H, s)
With methanol; potassium carbonate; at 20.0℃; for 1.5h;
(2) Potassium carbonate (29.7 g) was added to a solution of 6-trimethylsilanylethynylbenzothiazol (45.1 g) in methanol (600 ml), and the mixture was stirred for 1.5 hours at room temperature. The reaction solution was filtered, and then the resultant was washed with methanol and ethyl acetate successively. The filtrate was concentrated, to which water was added, and then extracted with ethyl acetate. The organic layer, which was washed with a brine, was dried over anhydrous magnesium sulfate. After the solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 ? 1:1) to yield 6-ethynylbenzothiazole (30.0 g) as a light yellow solid (mp: 47.5-49.0C). 1H NMR (300 MHz, CDCl3) delta ppm: 3.16 (1H, s), 7.63 (1H, dd, J = 8.4, 1.6 Hz), 8.08 (1H, dd, J = 8.5, 0.6 Hz), 8.11 (1H, d, J = 1.4 Hz), 9.04 (1H, s)
With triethylamine;tetrakis(triphenylphosphine) palladium(0); In acetonitrile; for 3.0h;Heating / reflux;
(2) To a solution of <strong>[864376-04-5]6-ethynylbenzothiazole</strong> (402 mg) synthesized in Example 17-(2) and 2-iodo-4-trifluoromethylthiazole (708 mg) in acetonitrile (8 ml), triethylamine (12.5 ml) and tetrakis(triphenylphosphine)palladium (151 mg) were added under nitrogen atmosphere, and then was heated under reflux for 3 hours under nitrogen atmosphere. After the solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=85:15?70:30) to yield the title compound (573 mg) as a yellow powder (mp: 153.0-154.0C). 1H NMR (300 MHz, CDCl3) delta ppm: 7.74 (1H, dd, J = 8.5, 1.6 Hz), 7.81 (1H, q, J = 0.9 Hz), 8.16 (1H, dd, J = 8.5, 0.6 Hz), 8.24 (1H, dd, J = 1.7, 0.6 Hz), 9.11 (1H, s)
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