Pyrrole → 2-tert-Butyl-5-(1H-pyrrol-1-ylsulfonyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole

Participants

Reaction Steps

Sodium hydride (139 mg, 60%, 3.5 mmol) was added to a solution of pyrrole (200 uL, 194 mg, 2.9 mmol) in THF (10 mL). Stirring for 3 h at room temperature, 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (185 mg, 0.5 mmol) was added. The reaction mixture was stirred overnight at room temperature, quenched with NH4Cl (5 mL), diluted with EtOAc (50 mL), washed with NaCl (2×20 mL) and dried over Na2SO4. The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 70 mg (35%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.36-1.53 (m, 4 H), 1.55 (s, 9 H), 2.18-2.38 (m, 1 H), 3.22-3.35 (m, 2 H), 3.88 (m, 2 H), 4.33 (d, J=7.42 Hz, 2 H), 6.22-6.31 (m, 2 H), 7.13-7.29 (m, 2 H), 7.71 (d, J=8.8 Hz, 1 H), 7.77 (dd, J=8.6, 1.8 Hz, 1 H), 8.13 (d, J=1.37 Hz, 1 H); MS (ESI) (M+H)+=401.8; Anal. Calcd for C21H27N3O3S+0.30H2O (406.94): C, 61.98; H, 6.84; N, 10.33. Found: C, 62.10; H, 6.90; N, 10.43.

Provenance & Evidence