4-Toluenesulfonyl chloride → HCID 11502228, compound

Participants

Reaction Steps

p-Toluenesulfonyl chloride (0.16 mmol) was added to a 0° C. solution of 6-(trifluoromethoxy)-1H-indazole-3-carboxylic acid (0.81 mmol) in pyridine. (5.00 mL). (3S)-Quinuclidin-3-ol (0.81 mmol) was added and the reaction mixture was allowed to warm to rt. The reaction mixture was maintained for 16 h and was filtered and concentrated. The residue was redissolved in methanol and loaded on a 5 g SCX column. The column was washed with methanol and the product was eluted with methanol/dimethylethylamine (9/1) and concentrated. The residue was purified by preparative HPLC to produce the desired product in 16% yield. Note: this procedure works equally well when p-toluenesulfonyl chloride is replaced with oxalyl chloride. 1H NMR (CDCl3) δ 8.52 (s, 1 H), 7.96 (d, J=8.9, 1H), 7.49 (s, 1 H), 7.09 (d, J=8.9, 1H), 5.31 (m, 1 H), 3.72-3.29 (m, 6 H), 2.56 (m, 1 H), 2.32 (m, 1 H), 2.06-1.88 (m, 3 H); LC/MS (EI) tR 4.9 min, m/z 356 (M++1).

Provenance & Evidence