反应详情

温度

80 °C

The bromopyridine 1 (1.4 g, 8.1 mmol), boronic acid 2 (2.0 g, 8.9 mmol) and potassium carbonate (2.2 g, 15.9 mmol) were dissolved in 80 mL toluene, 8 mL EtOH and 8 mL H2O. This mixture was evacuated and refilled with nitrogen several times. Then, tetrakistriphenylphosphine palladium (0) (350 mg, 0.30 mmol) was added to the mixture and the mixture was heated to 80° C. overnight. Water (100 mL) was then added to the reaction and the organic layer was partitioned. The aqueous layer was extracted with EtOAc (2×100 mL) and the combined organics were dried with Na2CO3 and concentrated. The crude reaction product was triturated with diethyl ether (25 mL) and filtered. The resulting solid (2.0 g, 83%) was collected and characterized as the biphenyl amine 3. 1H NMR (CDCl3): δ 8.17 (d, 1H), 8.03 (s, 1H), 7.45 (m, 2H), 7.25 (m, 2H), 6.55 (d, 1H), 4.50 (bs, 2H), 3.61 (m, 1H), 3.31 (m, 1H), 1.49 (d, 3H), 1.16 (d, 3H), 1.03 (d, 3H), 0.83 (d, 3H).

1. customThis mixture was evacuated
2. additionrefilled with nitrogen several times
3. customthe organic layer was partitioned
4. extractionThe aqueous layer was extracted with EtOAc (2×100 mL)
5. dry with materialthe combined organics were dried with Na2CO3
6. concentrationconcentrated
7. customThe crude reaction product
8. customwas triturated with diethyl ether (25 mL)
9. filtrationfiltered
10. customThe resulting solid (2.0 g, 83%) was collected