(Trifluoromethyl)trimethylsilane → 2-methyl-N-[2,2,2-trifluoro-1-(6-methylpyridin-2-yl)ethyl]propane-2-sulfinamide

HRID 1255856Notes

Reaction equation

[CH3:1][C:2]([S:5](/[N:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)=[O:6])([CH3:4])[CH3:3].C[Si](C)(C)[C:18]([F:21])([F:20])[F:19]>C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.C1C=CC([Si-](F)(F)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:4][C:2]([S:5]([NH:7][CH:8]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)[C:18]([F:21])([F:20])[F:19])=[O:6])([CH3:1])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 2-methyl-N-[(1E)-(6-methylpyridin-2-yl)methylene]propane-2-sulfinamide (0.33 g, 1.48 mmol) in THF (6 mL) was added to a dry flask containing TBAT (0.88 g, 1.63 mmol) and the solution was cooled to −78° C. under a nitrogen atmosphere. To this was added trimethyl(trifluoromethyl)silane (0.26 mL, 1.78 mmol) and the reaction was warmed to −20° C. for 2 hours. The reaction was quenched with ammonium chloride solution and partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (5-40% ethyl acetate/hexane) gave 2-methyl-N-[2,2,2-trifluoro-1-(6-methylpyridin-2-yl)ethyl]propane-2-sulfinamide. LC-MS EIMS: m/z 295.1 [M+H]+.

Workup

temperaturethe reaction was warmed to −20° C. for 2 hours
customThe reaction was quenched with ammonium chloride solution
custompartitioned between water and ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
customevaporated in vacuo
customPurification by flash chromatography (5-40% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-96c32fbf0fce41c69b503c538cc06697
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461162B2

Reaction notes

Loading…