Sodium Carbonate → 5-(Indazol-3-yl)-3-(1-Methylpiperidin-4-yl)-1H-Indole

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Reaction Steps

The title compound was prepared by the procedure of Example 14, beginning with 3-(1-methylpiperidin-4-yl)-1H-indole-5-boronic acid (0.250 g, 0.97 mmol), 3-chloro-1-(tert-butoxycarbonyl)indazole (0.230 g, 0.92 mmol), Pd(dppf)Cl2 CH2Cl2 (0.023 g, 0.028 mmol), and 2M aqueous sodium carbonate solution (2 mL) in 6 mL of tetrahydrofuran to give 0.197 g (47%) of 5-(3-[1-tert-butoxycarbonyl]indazolyl)-3-(1-methylpiperidin-4-yl)-1H-indole as an amorphous tan solid, which was dissolved in 3 mL of tetrahydrofuran, followed by the addition of sodium methoxide (0.074 g, 1.38 mmol) in 1 mL of methanol, and the mixture was allowed to stir at room temperature for 0.5 hours, followed by extractive work-up and silica gel chromatography to give 0.062 g (54%) of the title compound as an amorphous off-white solid. FDMS m/e=330 (M+). EA calculated for C21H22N4.½ H2O C, 74.31; H, 6.83; N, 16.50. Found: C, 74.52; H, 6.96; N, 15.95.

Provenance & Evidence