3-bromo-3,3-difluoroprop-1-ene → HCID 59295493, compound

HRID 2233296Notes

Reaction equation

HRID 2233296 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=2)[S:5][C:6]=1[CH:7]=[O:8].CC1N=C(C2C=N[C:30]([C:33](F)([F:35])[F:34])=[CH:31]C=2)SC=1CO.BrC(F)(F)C=C.[In]>CN(C)C=O>[F:34][C:33]([F:35])([CH:30]=[CH2:31])[CH:7]([C:6]1[S:5][C:4]([C:9]2[CH:10]=[N:11][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:14]=2)=[N:3][C:2]=1[CH3:1])[OH:8]

Participants

6

Reactant 4

HCID 5550853-bromo-3,3-difluoroprop-1-eneHCID 5359967IndiumHCID 59295400HCID 59295400, compoundHCID 59295476HCID 59295476, compound

Product 1

HCID 59295493HCID 59295493, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.0 g 4-Methyl-2-(6-trifluoromethyl-pyridin-3-yl)-thiazole-5-carbaldehyde (derived from [4-Methyl-2-(6-trifluoromethyl-pyridin-3-yl)-thiazol-5-yl]-methanol according to the method described for 4-Methyl-2-(trans-1,4-trifluoromethyl-cyclohexyl)-thiazole-5-carbaldehyde) and 4.33 g 3-bromo-3,3-difluorpropene in 25 ml dimethylformamide. 2.11 g Indium were added and the resulting suspension was stirred in an ultrasonic bath for three hours. Then 20 ml 1N HCL were added and the mixture stirred at room temperature for thirty minutes. The mixture was extracted three times with portions of 50 ml ethyl acetate. The combined organic layers were dried over MgSO4. The solvent was evaporated in vacuo. The resulting residue was purified by reversed phase HPLC to obtain 4.67 g 2,2-Difluoro-1-[4-methyl-2-(6-trifluoromethyl-pyridin-3-yl)-thiazol-5-yl]-but-3-en-1-ol as a colorless lyophilisate.

Workup

  1. additionThen 20 ml 1N HCL were added
  2. stirringthe mixture stirred at room temperature for thirty minutes
  3. extractionThe mixture was extracted three times with portions of 50 ml ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customThe solvent was evaporated in vacuo
  6. customThe resulting residue was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-a1ddf50102ef4a33bc87c208d996dba6
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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