Cesium carbonate → Tert-butyl (4-bromopyridin-2-yl)(2,2,2-trifluoroethyl)carbamate

HRID 632750Notes

Reaction equation

HRID 632750 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:28][C:29]([F:32])([F:31])[F:30])(=O)=O.[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]([CH2:28][C:29]([F:32])([F:31])[F:30])[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:3]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 11680626tert-butyl N-(4-bromopyridin-2-yl)carbamate

Product 1

HCID 118064935Tert-butyl (4-bromopyridin-2-yl)(2,2,2-trifluoroethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of tert-butyl (4-bromopyridin-2-yl)carbamate (1.5 g), cesium carbonate (2.7 g) and DMF (15 mL) was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (1.0 mL). The reaction mixture was stirred at room temperature for 15 hr, saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.0 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2716f975f5b145d2b2560c63f8e66ccd
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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