Potassium Phosphate, Tribasic → Tert-butyl 2-(3-nitro-5-(pyridin-4-yl)phenyl)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 2-(3-chloro-5-nitrophenyl)acetate 52.B (2.00 g, 7.36 mmol) and pyridin-4-ylboronic acid (1.09 g, 8.83 mmol) in t-amyl alcohol (20 mL) was added K3PO4 (4.69 g, 22.1 mmol), Pd2(dba)3 (337 mg, 0.368 mmol) and XPhos (702 mg, 1.47 mmol). The mixture was stirred for 3 hours at 100° C. and then was filtered over Celite. The liquid phase was concentrated and partitioned between water and AcOEt. The organic phase was then washed with brine, dried over MgSO4, concentrated and purified by flash chromatography on silica gel to afford tert-butyl 2-(3-nitro-5-(pyridin-4-yl)phenyl)acetate 52.0 (2.03 g, 72% yield).

Provenance & Evidence