Methyl 4-chloroacetoacetate → Methyl 2-(6,8-dibromoimidazo[1,2-a]pyridin-2-yl)acetate hydrochloride

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Reaction Steps

A mixture of 3,5-dibromopyridin-2-amine (9.03 g, 35.8 mmol) and methyl 4-chloro-3-oxobutanoate (2.0 g, 13 mmol) in THF (50 mL) was heated at reflux 48 hrs. The solid was filtered and dried to give methyl 2-(6,8-dibromoimidazo[1,2-a]pyridin-2-yl)acetate hydrochloride (1.48 g, 36% yield). LCMS B: 1.54 min (RT); (M+H)+=347.07 (75%), 349.07 (100%), 351.04 (75%). 1H NMR, 400 MHz, CDCl3: δ 9.01 (d, 1.4 Hz, 1 H), 8.38 (s, 1 H), 8.07 (d, 1.4 Hz, 1 H), 4.25 (s, 2 H), 3.40 (s, 3 H).

Provenance & Evidence