2,4-dichloro-N-{4-formyl-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide → 2,4-dichloro-N-{4-(cyclopropyl-hydroxy-methyl)-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide

Participants

Reaction Steps

A solution of cyclopropylmagnesium bromide (0.5 M, 1.55 ml, 0.78 mmol) was added to a stirred solution of 2,4-dichloro-N-{4-formyl-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide (130 mg, 0.22 mmol) in THF (15 ml) and the mixture stirred for 2 hours. The reaction was concentrated under reduced pressure onto silica and the residue purified by flash column chromatography using ethyl acetate 1/1 hexane as eluent to afford 2,4-dichloro-N-{4-(cyclopropyl-hydroxy-methyl)-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide as a green foam (74 mg, 54%). 1H NMR (CDCl3): 8.40 (1 H, s, py); 8.18 (1 H, d, Ar); 7.51 (3 H, m, py and Ar); 7.39 (1 H, s, py); 7.34 (1 H, d, Ar); 7.06 (2 H, d, Ar); 4.50 (1 H, d, CHOH); 2.89 (4 H, m, 2×CH2N pip); 1.54 (4 H, m, 2×CH2 pip); 1.34 (2 H, m, CH2 pip); 0.97 (1 H, m, CH cprop); 0.39 (4 H, m, 2×CH2 cprop).

Provenance & Evidence