Trifluoromethanesulfonyl chloride → HCID 66793888, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH2:9])[CH:5]=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[F:19][C:20]([F:26])([F:25])[S:21](Cl)(=[O:23])=[O:22]>ClCCl.C(=O)(O)[O-].[Na+].[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][S:21]([C:20]([F:26])([F:25])[F:19])(=[O:23])=[O:22])[CH:5]=[N:6][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 5-bromo-3-pyridinemethanamine (CAS#135124-70-8, 170 mg, 0.65 mmol) in dichloromethane (5 mL) at 0° C. was added diisopropylethylamine (0.55 mL, 3.25 mmol) and trifluoromethanesulfonyl chloride (0.083 mL, 0.78 mmol). The reaction was stirred at 0° C. for 15 minutes and then warmed to room temperature and stirred for an additional 30 minutes. The reaction was then diluted with saturated aqueous sodium bicarbonate and brine, and then further diluted with dichloromethane. The layers were separated and the aqueous layer was extracted two additional times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to provide N-(5-bromo-pyridin-3-ylmethyl)-C,C,C-trifluoro-methanesulfonamide with out the need for further purification. MS: (ES+) m/z 318.9 (M+H)+.
Workup
- temperaturewarmed to room temperature
- stirringstirred for an additional 30 minutes
- customThe layers were separated
- extractionthe aqueous layer was extracted two additional times with dichloromethane
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-23e05be709204461ad8219bc16562770
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778972B2
Reaction notes
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