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With sodium hydroxide; water; In methanol; at 50℃; for 4h;
To a solution of <strong>[162100-83-6]6-chloro-1H-indole-5-carboxylic acid methyl ester</strong> (6.0 g, 28.7 mmol) in 200 mL MeOH and 200 mL water was added NaOH (6.0 g) and the mix was heated at 50 C. for 4 h. The solution was cooled, diluted with water and acidified to pH 2-3 and extracted with EtOAc, washed with water and brine. The organic layer was dried with Na2SO4 and concentrated to give the desired product. M+H+(1196).
With sodium hydroxide; LiOH; In tetrahydrofuran; ethyl acetate;
EXAMPLE 58C 6-chloro-5-indolecarboxylic acid A solution of Example 58B (1.17 g, approximately 5.6 mmol) in THF (50 mL) was treated with 1M LiOH (56 mL, 56 mmol), heated at 50 C., stirred for 18 hours, treated with 1M NaOH, washed with diethyl ether, acidified with HCl, and extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated. The concentrate was purified on silica gel with 50% ethyl acetate/hexanes to provide of 660 mg of the desired product. 1H NMR (DMSO-d6) delta 12.73 (br s, 1H), 11.45 (s, 1H), 8.13 (s, 1H), 7.49 (m, 2H), 6.57 (m, 1H).
Isomer b was converted to 6-chloroindole-5-carboxylic acid using the same reaction sequence as described above and was coupled to 4-benzylpiperidine to obtain 6-chloro-5-(4-benzylpiperidinyl)-indole carboxamide as a white solid, MS (M+352).
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