Reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[S:8][C:9]=1[CH2:10][N:11]1[C:15]2=[N:16][CH:17]=[C:18]([OH:20])[CH:19]=[C:14]2[CH:13]=[CH:12]1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:37](Br)[CH:38]=[CH2:39].C(OCC)(=O)C>CN(C)C=O>[CH2:39]([O:20][C:18]1[CH:19]=[C:14]2[CH:13]=[CH:12][N:11]([CH2:10][C:9]3[S:8][C:7]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:30])[F:29])=[CH:23][CH:22]=4)=[N:6][C:5]=3[CH2:1][CH2:2][CH2:3][CH3:4])[C:15]2=[N:16][CH:17]=1)[CH:38]=[CH2:37]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
730 mg 1-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-1H-pyrrolo[2,3-b]pyridin-5-ol were dissolved in 20 ml dimethylformamide and 1.1 mg cesium carbonate and 410 mg allylbromide were added. The reaction mixture was stirred at room temperature for one hour then 100 ml ethyl acetate were added and the mixture was washed five times with portions of 20 ml of water The organic layer was dried over MgSO4 and the solvent removed under reduced pressure. This gives 800 mg 5-Allyloxy-1-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-1H-pyrrolo[2,3-b]pyridine as yellow oil.
Workup
- washthe mixture was washed five times with portions of 20 ml of water The organic layer
- dry with materialwas dried over MgSO4
- customthe solvent removed under reduced pressure
Sources & evidence
- ORD record
- ord-54927c94ecfd4e2981de3ebb5ba68007
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07541464B2
Linked notes
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