Sodium Carbonate → 6-[4-(Methylthio)phenyl]-3-pyridinol

Participants

Reaction Conditions

Reaction Steps

A mixture of [4-(methylthio)phenyl]boronic acid (7.2 g, 43.1 mmol), 6-bromo-3-pyridinol (5 g, 28.7 mmol), 2M Na2CO3 (44 mL), Pd(PPh3)4 (1.7 g, 1.4 mmol) and DME (70 mL) was degassed with N2 for 30 min, and stirred and heated at 80° C. for 18 h. The mixture was charged with water and CH2Cl2 and the organic layer was washed with 1N NaOH (100 mL). The basic aqueous layer was washed with Et2O, cooled in an ice bath and the pH was adjusted to about 10 with 6N HCl. The resulting solid was collected, washed with water and air-dried to give 6-[4-(methylthio)phenyl]-3-pyridinol (4.3 g, 69%) as a yellow solid. The reaction was repeated on twice the scale (10 g of 6-bromo-3-pyridinol) to provide 9.1 g (72%) of product. The reaction was repeated on 10× the scale (101.5 g of 6-bromo-3-pyridinol) to provide 53.7 g of product. 1H NMR (400 MHz, DMSO-d6): δ 9.96 (s, 1H), 8.15 (d, 1H, J=2.6 Hz), 7.87 (d, 2H, J=8.6 Hz), 7.73 (d, 1H, J=8.7 Hz), 7.27 (d, 2H, J=8.6 Hz), 7.18 (dd, 1H, Ja=8.6 Hz, Jb=2.9 Hz), 2.46 (s, 3H); LRMS (ESI), m/z 218 (M+H).

Provenance & Evidence