Cyclopropylboronic acid → HCID 57546172, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-(((3-bromo-5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (36 mg, 0.05 mmol), cyclopropylboronic acid (13 mg, 0.16 mmol), and tetrakis(triphenylphosphine) palladium(0) (6 mg, 0.005 mmol) were combined in dry tetrahydrofran (2 mL) in a microwave tube and sealed. The mixture was flushed with nitrogen then 180 μL of a 1 N potassium hydroxide aqueous solution was introduced. The mixture was heated at 100° C. for 1 h via microwave. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water (2×), then brine (2×), dried over sodium sulfate, and concentrated. Flash chromatography on silica gel (15% ethyl acetate/hexanes) gave 18 mg (53%). 1H-NMR (CDCl3, 500 MHz) δ 7.99 (s, 1H), 7.37 (s, 1H), 7.15-7.21 (m, 5H), 5.30 (s, 2H), 4.68 (s, 2H), 3.68 (m, 2H), 3.43 (s, 2H), 3.35-3.38 (m, 2H), 2.98-3.02 (m, 2H), 2.10-2.19 (m, 3H), 1.74-1.79 (m, 2H), 1.41 (s, 9H), 1.03-1.06 (m, 4H), 0.73-0.76 (m, 2H), 0.11 (s, 9H). Mass spec.: 660.31 (MH)+.

Provenance & Evidence