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

Beteiligte Stoffe

Reaktionsschritte

NaH (0.49 mg, 60%, 12.4 mmol) was a solution of 1H-Pyrrole-3-carbaldehyde (0.21 mg, 2.47 mmol) in THF (30 mL) at 0° C. The reaction mixture was allowed to warm to room temperature, stirred for 1 hour at room temperature and cooled down to 0° C. again. 2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (1.1 g, 20.97 mmol) was added slowly, allowed the reaction to warm to room temperature and stirred for 1 hour. The reaction mixture was quenched with NaHCO3 (5 mL), diluted with EtOAc (100 mL), washed with brine (2×15 mL) and dried over Na2SO4. The crude product was purified by MPLC on silica gel using Hexane/EtOAc (1:1) to give 0.44 g (34%) of a white solid as the title compound. 1H NMR (400 MHz, CHLOROFORM-D) δ 1.45-1.55 (m, 4 H), 1.56 (s, 9 H), 2.16-2.31 (m, 1 H), 3.25-3.35 (m, 2 H), 3.94-4.02 (m, 2 H), 4.22 (d, J=7.42 Hz, 2 H), 6.67 (dd, J=3.42, 1.66 Hz, 1 H), 7.18-7.22 (m, 1 H), 7.44 (d, J=8.79 Hz, 1 H), 7.76-7.82 (m, 2 H) 8.36 (d, J=1.76 Hz, 1 H) 9.79 (s, 1 H); MS (ESI) (M+H)+=430.00.

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