Sodium hydride → 1-{[2-(1,1-difluoroethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carbaldehyde

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Reaction Steps

Sodium hydride (0.55 mg, 60%, 13.8 mmol) was added to a solution of 1H-Pyrrole-3-carbaldehyde (0.26 g, 2.7 mmol) in 30 mL of THF at 0° C. After stirring for 1 h, 2-(1,1-difluoroethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (0.95 g, 2.5 mmol) was added. The reaction mixture was stirred for 3 h at 0° C., quenched with NaHCO3 (10 mL) and diluted with EtOAc (150 mL). The organic phases were washed with NaCl (2×20 mL) and dried over Na2SO4. The product was purified by normal-phase MPLC using Hex/EtOAc (1:1) to provide the title compound as a white solid. Yield: 0.86 g (79%); MS (ESI) (M+H)+=437.88.

Provenance & Evidence