1,3-Dibromopropane → (R)-methyl 2-(N-(3-bromopropyl)-4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylsulfonamido)propanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-methyl 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylsulfonamido)propanoate (200 mg, 0.30 mol) in MeCN (4 mL) were added K2CO3 (124 mg, 0.90 mol) and 1,3-dibromopropane (121 mg, 0.60 mol). The reaction flask was heated at 60° C. for 4 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was purified by column chromatography (silica, Hex/EtOAc, 1:1) to afford (R)-methyl 2-(N-(3-bromopropyl)-4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylsulfonamido)propanoate (113 mg, 47%) as a white foam. 1H NMR (400 MHz, CDCl3) δ 7.28 (d, 2H), 7.19 (s, 1H), 7.16-7.18 (d, 1H), 6.80-6.84 (t, 2H), 6.50-6.53 (m, 2H), 6.43-6.46 (m, 2H), 4.63-4.65 (q, 1H), 4.13 (s, 2H), 3.72 (s, 3H), 3.55 (s, 3H), 3.27-3.45 (m, 4H), 2.10-2.31 (m, 2H), 1.47 (s, 6H), 1.45 (s, 3H).

Provenance & Evidence