Epichlorohydrin → HCID 22293694, compound

HRID 967407Notes

Reaction equation

HRID 967407 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[CH:12][NH:11][N:10]=2)=[CH:5][CH:4]=1.[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[O:26]1[CH2:25][CH:24]1[CH2:22][N:11]1[CH:12]=[C:13]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:20])[F:21])=[CH:8][CH:7]=2)=[N:10]1

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 10796Cesium carbonateHCID 178506122HCID 178506122, compound

Product 1

HCID 22293694HCID 22293694, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[3-(4-trifluoromethyl-phenyl)-1H-pyrazol-4-yl]-pyridine (0.5 g, 1.73 mmol) and epichlorohydrin (1.35 mL, 17.3 mmol) in DMF (2 mL) was added cesium carbonate (0.676 g, 2.07 mmol). The reaction mixture was allowed to stir for 24 h, diluted with EtOAc and washed successively with saturated NaHCO3, water, and brine. The organic layer was dried over Na2SO4, concentrated and partially purified by running through a plug of silica gel (5% acetone/CH2Cl2) to afford 4-[1-oxiranylmethyl-3-(4-trifluoromethyl-phenyl)-1H-pyrazol-4-yl]-pyridine (0.198 g, 33%) as an unstable oil. TLC (silica, 20% acetone/CH2Cl2): Rf=0.39. MS (electrospray): exact mass calculated for C18H14F3N3O, 346.1 [M+H]+. m/z found, 346.1.

Workup

  1. washwashed successively with saturated NaHCO3, water, and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. custompartially purified

Sources & evidence

ORD record
ord-55fb8f7db6ee448fb8aca31644cf2273
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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