Sodium Carbonate → HCID 59331639, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of (S)—N-(3-(1-(6-chloropyrazin-2-ylamino)ethyl)phenyl)-3-(trifluoromethyl)benzamide (210 mg, 0.5 mmol), 4-(hydroxymethyl)phenylboronic acid (152 mg, 1 mmol) and aqueous sodium carbonate (0.62 mL, 2M, 1.55 mmol) in N,N-dimethyl formamide (3 mL) was added dichloro[1,1′-bis(diphenylphosphino)ferrocene)palladium(II) (24 mg, 0.03 mmol) and the mixture was heated at 80° C. for 18 hours in a sealed tube. After this time the mixture was allowed to cool, was poured into a mixture of brine/water (2:3, 50 mL) and was extracted with a mixture of ethyl acetate/tetrahydrofuran (4:1, 3×30 mL). The combined organic extracts were concentrated under reduced pressure and the residue was taken up in ethyl acetate (50 mL), dried (Na2SO4) and concentrated under reduced pressure to give a black oil which was purified by flash chromatography (silica, ethyl acetate/hexanes) to give (S)—N-(3-(1-(6-(4-(hydroxymethyl)phenyl)pyrazin-2-ylamino)ethyl)phenyl)-3-(trifluoromethyl)benzamide (80 mg, 33%) as a pale yellow solid.

Provenance & Evidence