Water → methyl 3-(3-chloro-2-methylbenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate

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Reaction Conditions

Reaction Steps

A mixture of methyl 2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate (200 mg, 0.72 mmol), prepared as described in Example 3, step f, 1-(bromomethyl)-3-chloro-2-methylbenzene (237 mg, 1.08 mmol) and Na2CO3 (153 mg, 1.44 mmol) in DMF (10 mL) was stirred at 80° C. for 5 h. It was cooled to room temperature and poured into water (100 mL). It was extracted with EA (100 mL×2). The combined organic layers were washed with brine (100 mL×3), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel eluted with MeOH/DCM=1/60 to afford the desired product as a black solid (239 mg, 80%); LC/MS: MS (ES+) m/e 415 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.39 (s, 3H), 2.44 (s, 3H), 3.42 (t, J=4.8 Hz, 4H), 3.69 (t, J=4.8 Hz, 4H), 3.92 (s, 3H), 5.45 (s, 2H), 6.37 (d, J=7.8 Hz, 1H), 7.07-7.12 (m, 2H), 7.36 (d, 1H).

Provenance & Evidence