Sodium Carbonate → HCID 90389218, compound

Participants

Reaction Steps

To a solution of tert-butyl 3-[bis(tert-butoxycarbonyl)amino]-5-bromo-1H-indazole-1-carboxylate (2.97 g, 5.81 mmol) in dimethoxyethane (25 mL) was added (5-chloro-2-hydroxyphenyl)boronic acid (1.00 g, 5.81 mmol), tetrakis(triphenylphosphine)palladium (0.67 g, 0.58 mmol) and 2 M aqueous sodium carbonate (5.8 mL, 11.6 mmol). The mixture was heated at refluxed for 5 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was diluted with ethyl acetate (50 mL), washed with water (2×20 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 30-60% gradient of ethyl acetate in hexanes to afford tert-butyl 3-[bis(tert-butoxycarbonyl)amino]-5-(5-chloro-2-hydroxyphenyl)-1H-indazole-1-carboxylate as a colorless solid in 84% yield (2.57 g): 1H NMR (300 MHz, DMSO-d6) δ8.21 (d, J=7.8 Hz, 1H), 7.62-7.59 (m, 2H), 7.46 (s, 1H), 6.90-6.86 (m, 2H), 5.33 (br s, 1H), 1.72 (s, 9H), 1.42 (s, 18H); MS (ES+) m/z 560.0 (M+1), 562.0 (M+1).

Provenance & Evidence