N-methyl-2-pyrrolidone → HCID 57552550, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 2-(3-fluoro-phenyl)-6-methoxy-naphthalen-1-ol (3.36 g, 12.5 mmol) in N-methyl-2-pyrrolidinone (NMP) (10 mL) and add sodium hydride (500 mg, 60% oil dispersion, 12.5 mmol) at room temperature. After stirring for 1 hour this solution is added to a solution of 4-fluorobenzaldehyde (2.4 mL, 22.5 mmol) in NMP (10 mL) that has been heated to 185° C. Continue stirring for 2.5 hours. Cool the reaction to room temperature and add pH 7 buffer (50 mL) and extract with ethyl acetate (2×100 mL). Wash the organic extracts with water and filter through a plug of silica gel. Purify the crude product using radial chromatography giving 2.50 g (54%) of the title compound and use without further purification: mass spectrum (ion spray) m/z=371 (M−H).

Provenance & Evidence