Ammonium Chloride → 1-(2-Chloro-5-fluoro-pyridin-4-yl)-3,3-diphenyl-propan-1-one

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Reaction Steps

At −70° C. to a solution of 2-chloro-5-fluoro-4-iodopyridine (873 mg) in THF (20 mL) was added n-butyllithium (2.2 mL, 1.6M in hexane) over a period of 15 min slowly. To that solution N-methoxy-N-methyl-3,3-diphenyl-propionamide (200 mg) in THF (8 mL) was added and stirring was continued at that temperature for 1 h. A saturated solution of NH4Cl was added, the mixture was diluted with EtOAc, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (CH2Cl2/n-heptane 1:2) to yield the title compound as a white solid, MS (ESI+): m/z=340.09 ([M+H]+, 1Cl).

Provenance & Evidence