3,5-Dibromopyridine → 4-(5-Bromo-3-pyridinyl)tetrahydro-2H-pyran-4-ol

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Reaction Conditions

Reaction Steps

To 3,5-dibromopyridine (592 mg, 2.50 mmol) in 2 mL of THF at −20° C. is added 1.3M i-PrMgCl_LiCl solution (1.83 mL, 2.4 mmol) in one portion. The mixture is allowed to stir for 30 min., warming to −10° C. The mixture is cooled to −20° C. and tetrahydro-pyran-4-one (0.23 mL, 3.00 mmol) is added. The reaction is quenched with 50 mL of saturated aqueous NH4Cl and diluted with 200 mL EtOAc. The organic phase is washed with 2×100 mL of H2O, 1×100 mL of brine. The organic phase is dried with MgSO4, filtered and concentrated. The crude material is applied to a silica column and purified (0-10% MeOH/CH2Cl2) to give 168 mg of 4-(5-bromo-pyridin-3-yl)-tetrahydro-pyran-4-ol.

Provenance & Evidence