Sodium Carbonate → 6-(4-(Methylsulfonyl)phenyl)pyridin-3-ol

Participants

Reaction Conditions

Reaction Steps

(4-Methylsulfonylphenyl)boronic acid (4.40 g, 21.55 mmol) was added to a solution of 6-bromo-3-pyridinol (2.5 g, 14.37 mmol) in DME (125 mL), followed by addition of 2M Na2CO3 (75 mL) and Pd(PPh3)4 (0.83 g, 0.72 mmol). The reaction mixture was degassed with N2 and heated at 80° C. overnight, then cooled to ambient temperature. Water (50 mL), 1N NaOH (50 mL), brine (50 mL) and CH2Cl2 (150 mL) were added. The CH2Cl2 layer was separated and the aqueous layer was washed with CH2Cl2 (100 mL). The combined CH2Cl2 extract was further washed with a mixture of water (50 mL), 1N NaOH (50 mL) and brine (50 mL). The aqueous layers were combined and washed with CH2Cl2 (100 mL), neutralized with concentrated HCl and extracted with EtOAc (250 mL×2). The combined EtOAc extract was filtered through celite on top of a layer of silica gel, which was further washed with EtOAc (100 mL). The EtOAc filtrate was washed with brine and dried over Na2SO4, filtered, and concentrated to a light yellow solid, which was triturated with small amount of hot MeOH to give 2.20 g (61%) of 6-[4-(methylsulfonyl)phenyl]-3-pyridinol as a white solid.

Provenance & Evidence