Potassium Phosphate, Tribasic → HCID 59631571, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 5-bromo-2-chloropyridin-3-amine (0.39 g, 1.9 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.48 g, 2.3 mmol), ground 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl, (S-Phos) (0.15 g, 0.37 mmol), palladium (II) acetate (42.9 mg, 0.19 mmol), and potassium phosphate tribasic (1.20 g, 5.7 mmol) in DMF (9 mL) and water (0.4 mL) was purged 3 times with argon and placed under vacuum 3 times. The reaction mixture was carefully heated to 90° C. After 4.5 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 using silica gel chromatography (0-100% EtOAc in hexanes) to afford a light yellow solid as 2-chloro-5-(3,6-dihydro-2H-pyran-4-yl)pyridin-3-amine. 1H NMR (400 MHz, CDCl3) δ ppm 7.87 (1H, d, J=1.8 Hz), 7.05 (1H, m), 6.16 (1H, m), 4.32 (2H, q, J=2.9 Hz), 3.93 (2H, t, J=5.5 Hz), 2.51 (2H, m). 2,5-bis(3,6-dihydro-2H-pyran-4-yl)pyridin-3-amine was also isolated. 1H NMR (400 MHz, CDCl3) δ ppm 8.13 (1H, d, J=2.0 Hz), 7.11 (1H, br. s.), 6.34 (2H, m), 4.46 (4H, m), 4.20 (6H, m), 2.67 (2H, m), 2.55 (2H, m). Mass Spectrum (pos.) m/e: 259.1 (M+1).

Provenance & Evidence