(Trifluoromethyl)trimethylsilane → N-(1-(5-bromopyridin-3-yl)-2,2,2-trifluoroethyl)-2-methylpropane-2-sulfinamide

HRID 1897824Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[N:9][S:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])[CH:5]=[N:6][CH:7]=1.[F:16][C:17]([Si](C)(C)C)([F:19])[F:18]>CCCC[N+](CCCC)(CCCC)CCCC.C1C=CC([Si-](F)(F)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:9][S:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])[C:17]([F:19])([F:18])[F:16])[CH:5]=[N:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of N-((5-bromopyridin-3-yl)methylene)-2-methylpropane-2-sulfinamide (10.75 mmol) and tetrabutylammonium difluorotriphenylsilicate(IV) (6.38 g, 11.83 mmol) in THF (53.8 ml) was cooled to −78° C. Then (trifluoromethyl)trimethylsilane 2M solution in THF (6.45 ml, 12.90 mmol) was added dropwise, and the mixture stirred at −78° C. for 2 h. Brine was added and the precipitate removed and washed with AcOEt. The filtrates were dried over MgSO4, filtered and concentrated. The residue was purified via Biotage (0-15% MeOH/CH2Cl2; SNAP50 column) giving the title compound (2.96 g, 77%) as a light yellow solid. LC-MS (M+1) 361.0.

Workup

customthe precipitate removed
washwashed with AcOEt
dry with materialThe filtrates were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified via Biotage (0-15% MeOH/CH2Cl2; SNAP50 column)

Sources & evidence

ORD record: ord-db54a63303824f36b1a250cfa2b6aaeb
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519142B2

Reaction notes

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