2-(2,4-Difluoro-phenyl)-6-methoxy-naphthalene-1-carbaldehyde → HCID 11192515, compound

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Reaction Conditions

Reaction Steps

Dissolve (4-bromo-phenyl)-(2-piperidin-1-yl-ethyl)-carbamic acid tert-butyl ester in dry tetrahydrofuran (20 mL). Cool to −78° C. and add 1.6 M n-butyl lithium in hexanes (0.79 mL). After 30 minutes, add 2-(2,4-difluoro-phenyl)-6-methoxy-naphthalene-1-carbaldehyde (0.25 g, 0.839 mmol) and stir 45 minutes cold. Warm to room temperature over 1 hour. Reflux 2 hrs. Cool to room temperature and dilute with dichloromethane (20 mL) and saturated aqueous ammonium chloride (20 mL). Separate the organic layer and wash the aqueous layer twice with dichloromethane. Combine the organics and dry over magnesium sulfate. Filter and concentrate in vacuo. Purify the residue by column chromatography using a silica gel column eluting with a linear gradient beginning with dichloromethane and ending with 4:1 dichloromethane methanol to give 0.45 g (92%) of the title compound: mass spectrum (ion spray) m/z=583.3 (M+H).

Provenance & Evidence