Cesium carbonate → HCID 86716008, compound

Temperature

100 °C

PdOAc2 (22 mg, 0.1 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)-biphenyl (53 mg, 0.13 mmol) (DavePhos), cesium carbonate (880 mg, 2.70 mmol) and potassium trifluoro(vinyl)borate (145 mg, 1.1 mmol) were mixed. THF (10 ml), water (3 ml) and 5-bromo-2-(1,1-difluoroethyl)pyrimidine (200 mg, 0.897 mmol) was added. Degassed for 20 minutes, with argon. The resulting mixture was capped and heated to 100° C., for 30 min in microwave oven. The reaction mixture was partitioned between EtOAc (20 mL) and H2O (10 mL). The aq. layer extracted with EtOAc (2×10 mL) and the combined organic layers washed with brine (10 mL), dried (Na2SO4) and concentrated. The reaction was purified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1) to afford 2-(1,1-difluoroethyl)-5-vinylpyrimidine (114 mg, 75% yield). 1H NMR (CDCl3 500 MHz): δ 8.88 (s, 2H), 6.73 (m, 1H), 6.02 (d, 1H), 5.61 (d, 1H), 2.10 (t, 2H).

1. customDegassed for 20 minutes, with argon
2. customThe resulting mixture was capped
3. customThe reaction mixture was partitioned between EtOAc (20 mL) and H2O (10 mL)
4. extractionThe aq. layer extracted with EtOAc (2×10 mL)
5. washthe combined organic layers washed with brine (10 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated
8. customThe reaction was purified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1)

ORD record

ord-126baa2979dc40c0b83630e1d8bccb72

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108938B2