Sodium Carbonate → HCID 22241318, compound

Participants

Reaction Conditions

Reaction Steps

A solution of phenylboronic acid (74.0 mg, 0.607 mmoles), ethyl 2-[3-(6-chloropyridin-2-ylmethoxy)-phenoxymethyl]-6-methylbenzoate (250 mg, 0.607 mmoles, example 6v), and sodium carbonate (77.8 mg, 1.21 mmoles) in 1:1H2O:AcCN (8 mL) is stirred under vacuum for five minutes. The reaction is placed under nitrogen, and tetrakis(triphenylphosphine)-palladium(0) (60.7 mg) is added followed by heating to 90° C. After two hours, another portion (15 mg) of phenylboronic acid is added. After another hour heating is stopped. Distilled water (10 mL) is added, followed by extraction with methylene chloride (twice with 20 mL). The organic extracts are combined and concentrated, and the resulting residue is purified by column chromatography (silica, 6:1 hex:EtOAc) to yield the title compound. MS (ESI) 454 (M+H)+.

Provenance & Evidence