Morpholine → HCID 59138644, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-(5-bromothiophen-2-yl)-3-(3-fluorophenyl)-2,2-dimethyl-propanoate, product of Preparation 1, Step 2, (367 mg, 0.988 mmol), morpholine (0.572 mL), palladium acetate (44 mg, 0.20 mmol), 2-(di-tert-butylphosphino)-biphenyl (118 mg, 0.40 mmol), and sodium tert-butoxide (228 mg, 2.37 mmol) in toluene (5 ml) was heated at 80° C. for 2 h. The reaction mixture was cooled to room temperature, the solid was removed by filtration, and the filtrate was concentrated in vacuo. The crude product was purified by silica gel flash chromatography using 20% ethyl acetate in hexanes to give methyl 3-(3-fluorophenyl)-2,2-dimethyl-3-(5-morpholinothiophen-2-yl)propanoate as an oil (120 mg, 32.2%). LC/MS (m/z) 378.33 [(M+H)+]; HPLC Rt: 3.548 min.

Provenance & Evidence