Cesium carbonate → HCID 90204110, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-Bromo-4-cyclopropylmethoxy-pyridine-2-carbonitrile (Example 53c, 150 mg, 593 μmol) in dry toluene (3.95 ml) under an argon atmosphere in a microwave vial were added 3,3-difluoroazetidine hydrochloride (CAN 288315-03-7, 84.4 mg, 652 μmol), palladium(II) acetate (13.3 mg, 59.3 μmol), BINAP (36.9 mg, 59.3 μmol) and cesium carbonate (386 mg, 1.19 mmol). The reaction mixture was stirred at 120° C. for 45 minutes under microwave radiation. The reaction mixture was filtered over a pad of celite and the filtrate was concentrated in vacuo. The residue was dissolved in ethylacetate and extracted with an aqueous solution of 1.0M sodium bicarbonate. The organic phase was collected, dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient to yield the title compound (157 mg, 79%) as a white solid. MS (ESI, m/z): 266.2 (M+H+).

Provenance & Evidence