Potassium Phosphate, Tribasic → 1,1-Dimethylethyl N-[(1S)-2-[[2-methoxy-5-(1H-pyrazol-4-yl)-3-pyridinyl]amino]-2-oxo-1-(phenylmethyl)ethyl]carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-tert-butyl 1-(5-bromo-2-methoxypyridin-3-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 15.1.B (1.00 g, 2.22 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole (0.52 g, 2.66 mmol, available from Aldrich) in t-amyl alcohol (20 mL) was added K3PO4 (1.41 g, 6.66 mmol), Pd2(dba)3 (102 mg, 0.111 mmol) and XPhos (212 mg, 0.444 mmol). The mixture was stirred for 4 hours at 100° C. and then was filtered over celite. The organic phase was concentrated and purified by flash chromatography on silica gel to afford tert-butyl (S)-1-(2-methoxy-5-(1H-pyrazol-4-yl)pyridin-3-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 15.1.C.

Provenance & Evidence