Dichloromethane → 4-[(4-Benzo[b]thien-7-yl-6-fluoro-3-pyridinyl)methyl]morpholine

Participants

Reaction Conditions

Reaction Steps

Combine 4-(6-fluoro-4-iodo-pyridin-3-ylmethyl)-morpholine (0.48 g, 1.5 mmol), 2-benzo[b]thiophen-7-yl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (0.47 g, 1.8 mmol) and sodium carbonate (0.39 g, 3.75 mmol) in CH3CN (8 mL) and water (4 mL). Purge the mixture with nitrogen for 5 min. Add [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (5.0 mg, 0.6 mmol) and purge with nitrogen for an additional 5 min. Heat the mixture at 120° C. for 10 min in microwave reactor and cool to room temperature. Dilute the reaction mixture with ethyl acetate, wash with water and saturated aqueous sodium chloride. Separate the organic layer and dry over magnesium sulfate. Filter and concentrate in vacuo to give a crude mixture. Purify by column chromatography (0.1% to 1% 2 M ammonia in methanol/dichloromethane) to afford the title compound (0.43 g, 87%). MS (ES) m/z 329 [M+1]+.

Provenance & Evidence