Cyclopropylboronic acid → (+/-)-tert-Butyl 4-((1-(5-chloro-3-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate

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(±)-tert-Butyl 4-((1-(3-bromo-5-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate (100 mg, 0.14 mmol), cyclopropylboronic acid (18.5 mg, 0.22 mmol), and tetrakis(triphenylphosphine) palladium(0) (16.6 mg, 0.01 mmol) were combined in dry tetrahydrofuran (3 mL) in a microwave tube and sealed. The mixture was flushed with nitrogen then 0.5 mL 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 65 mg (69%). 1H-NMR (CDCl3, 500 MHz) δ 7.58 (d, J=1.8 Hz, 1H), 7.21-7.23 (m, 2H), 6.97-7.01 (m, 3H), 5.50 (qAB, JAB=11.9 Hz, 2H), 5.00 (q, J=6.4 Hz, 1H), 3.69 (m, 2H), 3.33-3.45 (m, 2H), 3.19-3.27 (m, 2H), 3.01-3.06 (m, 2H), 2.01-2.14 (m, 3H), 1.79-1.89 (m, 2H), 1.43 (s, 9H), 1.41 (m, 3H), 0.96-1.01 (m, 4H), 0.67-0.83 (m, 2H), 0.09 (s, 9H). Mass spec.: 658.67 (MH)+.

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