反应详情

温度

80 °C

A mixture of 2-bromo-5-fluoro-3-methyl-pyridine (190 mg, 1.0 mmol), benzhydrylidene-hydrazine (216 mg, 1.1 mmol), phenylboronic acid (5 mol %, 6 mg) and potassium tert-butoxide (157 mg, 1.4 mmol) in anhydrous toluene (6 mL) was degassed with a stream of argon, treated with Pd(OAc)2 (2 mol %, 5 mg) and racemic (1,1′-binaphthalene-2,2′-diyl)bis(diphenylphosphine) (2 mol %, 12 mg) and stirred at 80° C. for 1 h. After cooling to RT, the reaction mixture was diluted with EtOAc and washed with water followed by a saturated aqueous solution of NaHCO3. The organic layer was dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by FCC on silica, using a gradient of 1-10% MeOH in DCM followed by 100% DCM, to afford the title compound (196 mg, 64%). LCMS (Method 4): Rt 3.44 min, m/z 306 [MH+].

1. customwas degassed with a stream of argon
2. additiontreated with Pd(OAc)2 (2 mol %, 5 mg) and racemic (1,1′-binaphthalene-2,2′-diyl)bis(diphenylphosphine) (2 mol %, 12 mg)
3. temperatureAfter cooling to RT
4. additionthe reaction mixture was diluted with EtOAc
5. washwashed with water
6. dry with materialThe organic layer was dried (MgSO4)
7. concentrationconcentrated in vacuo
8. customThe resultant residue was purified by FCC on silica