2-Bromo-5-fluoropyridine → HCID 86637811, compound

Participants

Reaction Conditions

Reaction Steps

Pd(PPh3)4 (230 mg, 0.20 mmol) was added to a solution of 2-bromo-5-fluoropyridine (350 mg, 2.0 mmol), 2-(4-bromophenyl)cyclopent-1-ene-1-carbaldehyde (500 mg, 2.0 mmol) and hexamethylditin (652 mg, 2.0 mmol) in degassed 1,4-dioxane (10 mL) at ambient temperature. After stirring at 110° C. for a further 3 days, the reaction mixture was diluted with diethyl ether and CsF/celite (1:1) was added. After stirring vigorously for 1 hr, reaction mixture was filtered and concentrated. Chromatography over silica eluting with 0-20% ethyl acetate/hexane afforded 2-[4-(5-fluoropyridin-2-yl)phenyl]cyclopent-1-ene-1-carbaldehyde as an orange gum.

Provenance & Evidence