Water → HCID 117770714, compound

HRID 1526287Notes

Reaction equation

HRID 1526287 reaction equation
Br[C:2]1[CH:7]=[N:6][C:5]([Br:8])=[CH:4][N:3]=1.Cl.[F:10][C:11]1([F:17])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[Br:8][C:5]1[CH:4]=[N:3][C:2]([N:14]2[CH2:15][CH2:16][C:11]([F:17])([F:10])[CH2:12][CH2:13]2)=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27583514,4-Difluoropiperidine hydrochlorideHCID 114704212,5-dibromopyrazine

Product 1

HCID 117770714HCID 117770714, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2,5-dibromopyrazine (200 mg), 4,4-difluoropiperidine hydrochloride (132 mg) and cesium carbonate (603 mg) in dimethyl sulfoxide (5 mL) was stirred overnight at 90° C. under nitrogen atmosphere. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (89 mg).

Workup

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

Sources & evidence

ORD record
ord-3fa9fc939a674b3caf664c78d8c36868
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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