2,4-Dimethoxybenzylamine → 3-Chloro-7-[[(2,4-dimethoxyphenyl)methyl]amino]-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

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Reaction Conditions

Reaction Steps

7-bromo-3-chloro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (3.0 g, 9.40 mmol), tris(dibenzylideneacetone) dipalladium (0) (Pd2(dba3)) (43 mg, 0.047 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (BINAP) (88 mg, 0.141 mmol), and sodium tert-butoxide (1.08 g, 11.3 mmol) were combined in a dry flask through which argon was purged. The flask was charged with 100 mL of dry dioxane, 2,4-dimethoxybenzylamine (1.41 mL, 9.40 mmol) was added, and the mixture was sparged with argon for 5 minutes. The reaction was heated to 100° C. and stirred under argon. After 2 h the reaction was concentrated and dissolved in 400 ml of ethyl acetate and washed with 100 mL of saturated aqueous ammonium chloride solution. The organic layer was separated, dried with magnesium sulfate, filtered, and concentrated. The resultant solids were slurried in 50 mL hot methanol, then allowed to cool to ambient temperature. The solids were filtered and dried to afford the title compound. LRMS (APCI) calculated for C23H20ClN2O3 [M+H]+, 407.1; found 407.1.

Provenance & Evidence