Water → 4-bromo-2-methyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-nitro-1H-benzo[d]imidazole

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Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-methyl-6-nitro-1H-benzo[d]imidazole (22 g, 78 mmol), prepared as described in example 1, step b, 1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene (22 g, 86 mmol) and cesium carbonate (38 g, 117 mmol) in DMF (400 mL) was stirred at 80° C. for 3 h. After cooled to room temperature, the mixture was poured into 300 mL of water and extracted with ethyl acetate (200 mL×3). The combined organic layers were washed with brine, dried over sodium sulphate and combined with a separate batch prepared similarly and then evaporated to give the crude product (55 g, 62%) as a yellow solid; LC/MS: MS (ES+) m/e 428 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 2.54 (s, 3H), 2.55 (s, 3H), 5.78 (s, 2H), 6.35 (d, J=7.8 Hz, 1H), 7.25 (t, J=7.8 Hz, 1H), 7.63 (d, J=7.8 Hz, 1H), 8.31 (d, J=1.5 Hz, 1H), 8.63 (d, J=1.5 Hz, 1H).

Provenance & Evidence