Triethylamine → HCID 57546045, compound

Participants

Reaction Conditions

Reaction Steps

(5-Chloro-2-cyclopropyl-2H-indazol-7-yl)methanol (0.39 g, 1.75 mmol) and triethylamine (0.73 mL, 5.25 mmol) were combined in dimethyl sulfoxide (4 mL) and cooled to 0° C. The reaction was treated with sulfur trioxide pyridine complex (0.87 g, 5.25 mmol) in dimethyl sulfoxide (2 mL), stirred at 0° C. for 5 min, and at room temperature for 20 min. The reaction was poured into ice water and extracted with ethyl acetate (2×). The organic layers were pooled together, washed with 10% acetic acid (2×), water (2×), saturated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (30% ethyl acetate/hexanes) gave 298 mg (77%) as a yellow solid. 1H-NMR (CDCl3, 300 MHz) δ 10.52 (s, 1H), 8.05 (s, 1H), 7.84 (d, J=2.2 Hz, 1H), 7.77 (d, J=1.8 Hz, 1H), 3.96-4.03 (m, 1H), 1.35-1.40 (m, 2H), 1.16-1.23 (m, 2H). Mass spec.: 221.30 (MH)+.

Provenance & Evidence