Thionyl Chloride → HCID 53309971, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-(5-hydroxy-3-phenyl-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)methanesulfonamide (40 mg, 0.11 mmol) in CH2Cl2 (2 mL) was added SOCl2 (30 uL, 0.41 mmol) at 0° C. The mixture was left to stir at 0° C. for 1 h and concentrated in vacuo. To the residue were added CH2Cl2 (2 mL) and pyrrolidine (0.10 mL, 1.2 mmol) at 0° C. The mixture was allowed to warm to room temperature as the bath did, and left to stir overnight. The mixture was concentrated and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CD3OD) δ 8.83 (s, 1H); 7.91 (s, 1H); 7.15-7.64 (m, 10); 4.31 (br s, 1H); 3.02 (s, 3H); 2.09 (br s, 4H); 1.61 (br s, 4H). LRMS (APCI) calc'd for (C25H26N3O2S) [M+H]+, 432.2; found 432.1.

Provenance & Evidence