Sodium Carbonate → 5-(3,6-dihydro-2H-pyran-4-yl)pyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 3-amino-5-bromopyridine (0.25 g, 1.4 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.33 g, 1.6 mmol), tetrakis(triphenylphosphine)palladium (83.3 mg, 0.072 mmol), and 2.0M sodium carbonate (3.6 mL, 7.2 mmol) in toluene (3.0 mL) and EtOH (1.0 mL) was heated to 70° C. After 19 h, the reaction was cooled to rt then diluted with water. After extraction with EtOAc, the organic extraction was dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified on basic alumina (0-35% EtOAc in hexanes) to afford a white solid as 5-(3,6-dihydro-2H-pyran-4-yl)pyridin-3-amine. 1H NMR (500 MHz, CDCl3) δ ppm 8.05 (1H, d, J=2.0 Hz), 7.96 (1H, d, J=2.7 Hz), 6.95 (1H, m), 6.10 (1H, tt, J=2.9, 1.5 Hz), 4.28 (2H, q, J=2.9 Hz), 3.90 (2H, t, J=5.5 Hz), 3.81 (1H, br. s.), 2.48 (2H, m). Mass Spectrum (pos.) m/e: 177.1 (M+1).

Provenance & Evidence