Dimethyl Sulfoxide → 6-Formylpyridine-3-carbonitrile

Temperature

-78 °C

Oxalyl chloride (936 mg, 7.38 mmol) is dissolved in dichlormethane (8 ml) under an argon atmosphere and cooled to −78° C. in an acetone dry-ice bath. Dimethylsulfoxide (1.153 g, 14.76 mmol) is added dropwise and the mixture is stirred for 20 minutes at −78° C. The compound of Example 32A (900 mg, 6.71 mmol) is added dropwise as a dichloromethane (7 ml) solution. The reaction is stirred for an additional two hours at −78° C. Triethylamine (3.05 g, 30.19 mmol) is added and the reaction is kept at −78° C. for 10 minutes, then allowed to warm to room temperature. The reaction is quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The ethyl acetate phase is washed with bicarbonate and brine, dried over magnesium sulphate monohydrate, filtered and concentrated to afford a yellow oil. The crude oil is purified by column chromatography on silica gel with dichloromethane as eluent.

1. stirringThe reaction is stirred for an additional two hours at −78° C
2. waitthe reaction is kept at −78° C. for 10 minutes
3. temperatureto warm to room temperature
4. customThe reaction is quenched with saturated ammonium chloride solution
5. extractionextracted with ethyl acetate
6. washThe ethyl acetate phase is washed with bicarbonate and brine
7. dry with materialdried over magnesium sulphate monohydrate
8. filtrationfiltered
9. concentrationconcentrated
10. customto afford a yellow oil
11. customThe crude oil is purified by column chromatography on silica gel with dichloromethane as eluent

ORD record

ord-45fae2136a694d9aa581ae177692beaa

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691854B2