2-Fluorophenylboronic acid → Tert-butyl 6-(2-fluorophenyl)nicotinate

温度

90 °C

To a round-bottom flask was added 2-fluoro phenylboronic acid (271 mg, 1.94 mmol), palladium tetrakis(triphenylphosphine) (22.4 mg, 0.0194 mmol)) and tert-butyl 6-bromonicotinate (500 mg, 1.94 mmol) and the mixture was evacuated 3× with N2. The solids were dissolved in 25 mL of DMF, followed by addition of 2.9 mL of 2 M cesium carbonate. The resulting mixture was heated to ˜90° C. The mixture was cooled to room temperature and then poured into a seperatory funnel, followed by addition of EtOAc and water (1×200 mL). The layers were separated and the organic extract washed with brine (1×200 mL), dried MgSO4, filtered and concentrated to afford an orange oil. The crude mixture was purified by chromatography (silica, 10% EtOAc:Heptane) to afford the desired product (224 mg, 40%). 1H NMR (400 MHz, DMSO-d6) □ ppm 9.16 (1H, d, J=2.2 Hz), 8.34 (1H, dd, J=8.3, 2.3 Hz), 7.90-8.05 (2H, m), 7.50-7.62 (1H, m), 7.33-7.44 (2H, m) 1.59 (9 H, s).

1. customthe mixture was evacuated 3× with N2
2. dissolutionThe solids were dissolved in 25 mL of DMF
3. additionfollowed by addition of 2.9 mL of 2 M cesium carbonate
4. temperatureThe mixture was cooled to room temperature
5. additionpoured into a seperatory funnel
6. additionfollowed by addition of EtOAc and water (1×200 mL)
7. customThe layers were separated
8. extractionthe organic extract
9. washwashed with brine (1×200 mL), dried MgSO4
10. filtrationfiltered
11. concentrationconcentrated
12. customto afford an orange oil
13. customThe crude mixture was purified by chromatography (silica, 10% EtOAc:Heptane)

ORDレコード

ord-be25294b13c34883baf5e1c4cbf140ff

出典データセット

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07902373B2