Triethylamine → Ethyl 6-chloro-7-(4-(6-(2,4-difluorophenyl)pyridin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

Ethyl 7-(4-(6-bromopyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate (Example 52, Step A, 40 mg, 0.0752 mmol), 2,4-difluorophenylboronic acid (15.4 mg, 0.0978 mmol), and cesium fluoride (29.7 mg, 0.196 mmol) in i-PrOH (1 ml) were sparged with argon for 2 minutes in a vial. Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (3.09 mg, 0.00376 mmol) and triethylamine (15.7 μl, 0.113 mmol) were added and the vial capped. The reaction was heated to 105° C. for 90 minutes. The reaction was applied directly to a silica gel column and eluted with 20 to 80% ethyl acetate/hexanes gradient to provide the title compound (30 mg, 0.0531 mmol, 70.6% yield) as a white foam.

Provenance & Evidence