Potassium Phosphate, Tribasic → 2-(6-Methoxypyridin-3-yl)-5-morpholinoaniline

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 2-chloro-5-morpholinoaniline (608 mg, 2.86 mmol), grounded 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl, (S-Phos) (236 mg, 0.57 mmol), palladium (II) acetate (64.7 mg, 0.29 mmol), 6-methoxypyridin-3-ylboronic acid (876 mg, 5.72 mmol), and potassium phosphate tribasic (1.82 g, 8.59 mmol) in DMF (7.0 mL) and water (0.3 mL) was purged 3 times with argon and placed under vacuum 3 times. The reaction mixture was carefully heated to 90° C. After 21 h, the reaction was cooled to rt, then diluted with water and extracted 3 times with EtOAc. The organic extractions were combined and washed twice with brine. After drying over anhydrous sodium sulfate and filtration, the organic solvent was removed under reduced pressure. The residue was purified over basic alumina (0-20% EtOAc in hexanes) to afford a tan solid as 2-(6-methoxypyridin-3-yl)-5-morpholinoaniline. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.12 (1H, d, J=1.8 Hz), 7.69 (1H, dd, J=8.6, 2.5 Hz), 6.92 (2H, m), 6.34 (1H, d, J=2.3 Hz), 6.28 (1H, dd, J=8.4, 2.5 Hz), 4.68 (2H, s), 3.87 (3H, s), 3.78 (4H, m), 3.12 (4H, m). Mass Spectrum (pos.) m/e: 286.1 (M+1).

Provenance & Evidence