Potassium Phosphate, Tribasic → 3-Pyridinol, 6-(phenylmethyl)-

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Reaction Conditions

Reaction Steps

In a sealed tube, a mixture of K3PO4 (16 g, 78 mmol), S-Phos (0.64 g, 1.6 mmol), and palladium acetate (0.29 g, 1.3 mmol) in THF (70 mL) was treated with 6-bromopyridin-3-ol (4.50 g, 26 mmol) and β-benzyl-9-BBN (0.5M solution in THF, 103 mL, 52 mmol). The mixture was heated to 80° C. for 18 h and diluted with EtOAc. The organic phase was washed with 2M aqueous NaOH, brine, dried over MgSO4, and concentrated. Purification by flash chromatography using EtOAc/hexanes gave 6-benzylpyridin-3-ol. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.66 (br. s, 1H), 8.03 (t, J=1.8 Hz, 1H), 7.13-7.30 (m, 4H), 7.07 (d, J=1.9 Hz, 2H), 3.95 (s, 2H). MS (ESI) m/z: Calculated; 185.1 Observed: 186.1 (M++1).

Provenance & Evidence