Sodium hydride → 4-Iodo-5-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole

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Reaction Steps

To a solution of 4-Iodo-5-methyl-1H-benzoimidazole (100 mg, 0.39 mmol, Example 287: step a) and SEMCl (71 mg 0.43 mmol) in 2 mL of DMF under Ar was added NaH (11 mg, 0.43 mmol). The mixture was stirred at RT for 4 h and purified directly by PTLC (25% EtOAc/hexane) to give 122 mg (81%) of product as a colorless oil: 1H-NMR (CDCl3; 400 MHz) δ 7.95 (s, 1H), 7.37 (d, 1H, J=8.4 Hz), 7.21 (d, 1H, J=8.4 Hz), 5.48 (s, 2H), 3.47 (t, 2H, J=8.3 Hz), 2.59 (s, 3H), 0.89 (t, 2H, J=8.3 Hz), −0.06 (s, 91H). Mass spectrum (ESI, m/z): Calcd. for C14H21IN2OSi, 389.1 (M+H), found 389.0.

Provenance & Evidence