Dimethyl Sulfoxide → 5-Bromo-α,α-dimethyl-3-pyridineacetaldehyde

Participants

Reaction Steps

A solution of oxalyl chloride in dichloromethane (2.0 M, 0.869 mL, 1.74 mmol) was diluted with dichloromethane (2 mL) and then a solution of dimethylsulfoxide (0.250 mL, 3.50 mmol) in dichloromethane (1 mL) was added at −78° C. After stirring for 15 minutes, a solution of the title compound from Example 53 Step E (0.200 g, 0.869 mmol) in dichloromethane (3 mL) was added. The resulting reaction stirred for 30 minutes before triethylamine (0.600 mL, 4.35 mmol) was added. The reaction warmed to room temperature slowly and stirred overnight. It was quenched with the addition of water and then extracted with dichloromethane. The combined organics were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel (25-100% ethyl acetate in hexanes) provided the title compound: LCMS m/z 229.87 [M+2H]+; 1H NMR (500 MHz, CDCl3) δ 9.53 (s, 1H), 8.61 (s, 1H), 8.47 (s, 1H), 7.73 (s, 1H), 1.51 (s, 6H).

Provenance & Evidence