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With potassium <i>tert</i>-butylate In 1-methyl-pyrrolidin-2-one at 20℃; for 18h;
79-2 Preparation Example 64-3: synthesis of 7-chloro-2-methyl-1H-indole-5-carboxylic acid methyl ester
General procedure: 4-Amino-3-chloro-5-prop-1-ynyl-benzoic acid methyl ester (1.7 g, 7.6 mmol) obtained from Preparation Example 64-2 was dissolved in N-methylpyrrolidone, and potassium t-butoxide (840 mg, 7.6 mmol) was slowly added dropwise thereto. The mixture was stirred for 18 hours at room temperature, added with 1N hydrochloric acid aqueous solution and extracted with ethyl acetate. The extract was washed with brine, dried with anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure. The residue was separated by column chromatography to obtain the title compound (1.4 g, 82%). [990] NMR: 1H-NMR (400HMz, CDCl3); δ 8.30(s, 1H), 8.17(s, 1H), 7.83(s, 1H), 6.35(s, 1H), 3.92(s, 3H), 2.49(s, 3H)
65.D methyl-7-chloro-5-indole-carboxylate
EXAMPLE 65D methyl-7-chloro-5-indole-carboxylate 5-Bromo-7-chloro-indole was processed as described in Example 63C to provide the desired product. MS (ESI(+)) m/z 210 (M+H)+and 227 (M+NH4)+; 1H NMR (CDCl3) δ 8.58 (s, 1H), 8.33 (s, 1H), 7.92 (d, J=l.1 Hz, 1H), 7.33 (m, 1H), 6.70 (dd, J=2.2, 2.9 Hz, 1H), 3.94(s, 3H).
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