Sodium hydride → methyl 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylate

Participants

Reaction Steps

Following the same procedure in Example 29, using methyl 1H-pyrrole-3-carboxylate (0.16 g, 1.3 mmol) (see following step B for preparation), sodium hydride (0.18 g, 60%, 4.5 mmol) and 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (0.48 g, 1.3 mmol) in THF (10 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 0.16 g (27%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.46-1.54 (m, 4 H), 1.56 (s, 9 H), 2.15-2.32 (m, 1 H), 3.25-3.37 (m, 2 H), 3.79 (s, 3 H), 3.93-4.03 (m, 2 H), 4.22 (d, J=7.42 Hz, 2 H), 6.62 (dd, J=3.32, 1.56 Hz, 1 H), 7.15 (dd, J=3.32, 2.34 Hz, 1 H), 7.42 (d, J=8.79 Hz, 1 H), 7.74-7.81 (m, 2 H), 8.33 (d, J=1.37 Hz, 1 H); MS (ESI) (M+H)+=459.8; Anal. Calcd for C23H29N3O5S+0.10 EtOAc+0.30H2O (474.98): C, 59.43; H, 6.45; N, 8.85. Found: C, 59.34; H, 6.60; N, 8.84.

Provenance & Evidence