Dichloromethane → 1-(5-Bromo-4-methylpyridin-2-yl)-2,2,2-trifluoroethane-1,1-diol
Reaction equation
[Br:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5]([CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10])=[N:6][CH:7]=1.ClCCl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:20].S([O-])([O-])(=O)=S.[Na+].[Na+]>>[Br:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5]([C:8]([OH:20])([OH:13])[C:9]([F:10])([F:11])[F:12])=[N:6][CH:7]=1Participants
5
Procedure
To a solution of 1-(5-bromo-4-methylpyridin-2-yl)-2,2,2-trifluoro-ethanol (345 mg; 1.2775 mmol) in dichloromethane (10 mL; 156.0 mmol) was added Dess-Martin periodinane (0.7313 g; 1.672 mmol). The reaction mixture was stirred at room temperature for 5 hours. 20 mL of a 10% aqueous solution of sodium thiosulfate was added and the reaction stirred for an additional 10 minutes. The reaction mixture was washed with 2 M aqueous sodium carbonate, dried over MgSO4, filtered, and concentrated. The crude product was carried forward without purification. LCMS (ESI): M+H=286.0; 1H NMR (400 MHz, DMSO) δ 8.70 (s, 1H), 7.72 (s, 1H), 7.59 (s, 2H), 2.43 (s, 3H).
Workup
- stirringthe reaction stirred for an additional 10 minutes
- washThe reaction mixture was washed with 2 M aqueous sodium carbonate
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was carried forward without purification
Sources & evidence
- ORD record
- ord-4a90361ccab0431bb280ae68c5c6ccdf
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08623889B2
Reaction notes
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