Sodium hydride → HCID 10251994, compound

Participants

Reaction Steps

To a solution of 0.50 g (1.79 mmol) of 3-(4-aminophenylmethyl) -5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine (Step B, Example 25) in 4.0 mL DMF, was added 143 mg (3.57 mmol, 2.0 eq) of a 60% oil dispersion of NaH. When evolution of hydrogen ceased (approximately 5 min.), 1.04 mL (5.36 mmol, 3.0 eq) of methyl 2-bromophenylacetate was added, and the mixture was stirred for 18 hours. The DMF was removed in vacuo and the resultant brown oil was flash chromatographed with 2:1 ethyl acetate/hexane to yield 0.690 g (90%) of a yellow-green powder.

Provenance & Evidence