Sodium Carbonate → HCID 22482418, compound

Participants

Reaction Conditions

Reaction Steps

To a well-stirred mixture consisting of the title compound of Step 1, this Example (1.40 g, 5.93 mmol), diethyl(3-pyridyl)borane (0.96 g, 6.53 mmol) and bis(triphenylphosphine) palladium (II) chloride (458 mg, 0.65 mmol) in tetrahydrofuran (15 ml), a 7.5 ml aqueous solution of sodium carbonate (2.51 g, 23.7 mmol) was added. The reaction mixture was then stirred at 90° C. for 5 hours, and then at ambient temperature for 18 hours. The aqueous phase of the biphasic reaction mixture is separated and extracted with an equal volume of ethyl acetate. The solvent of the organic phase of the reaction mixture was removed in vacuo and the residue is extracted with ethyl acetate (25 ml). The combined organic extracts are dried (anhydrous sodium sulfate) and concentrated in vacuo, yielding a dark viscous oil. Flash chromatography of the entire sample (silica gel, 47-61 micron mesh; elution with ethyl acetate) afford the title compound (807 mg, 58% yield) as a viscous yellow syrup.

Provenance & Evidence