Potassium Carbonate → methyl 5-(1H-imidazo[4,5-c]pyridin-1-yl)-3-{[2-(trifluoromethoxy)benzyl]oxy}thiophene-2-carboxylate
Reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Br.[OH:14][C:15]1[CH:19]=[C:18]([N:20]2[C:28]3[CH:27]=[CH:26][N:25]=[CH:24][C:23]=3[N:22]=[CH:21]2)[S:17][C:16]=1[C:29]([O:31][CH3:32])=[O:30].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:20]1([C:18]2[S:17][C:16]([C:29]([O:31][CH3:32])=[O:30])=[C:15]([O:14][CH2:6][C:5]3[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=3[O:3][C:2]([F:13])([F:12])[F:1])[CH:19]=2)[C:28]2[CH:27]=[CH:26][N:25]=[CH:24][C:23]=2[N:22]=[CH:21]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
110 mg of 2-(trifluoromethoxy)benzyl bromide is added to a mixture of 100 mg of methyl 3-hydroxy-5-(1H-imidazo[4,5-c]pyridin-1-yl)thiophene-2-carboxylate and 59.7 mg of potassium carbonate in 3 ml anhydrous DMF. The mixture is stirred for 14 h at room temperature. Ice water is added and the organic phase is extracted with dichloromethane. The organic phase is poured on a phase separator and the solvent is removed under vacuum. The residue is dissolved in 2 ml of dichloromethane and filtered through a short plug of silica gel (eluent: hexane/ethyl acetate 1/1 (v/v) to 0/100 (v/v)) to yield the title compound.
Workup
- extractionthe organic phase is extracted with dichloromethane
- additionThe organic phase is poured on a phase separator
- customthe solvent is removed under vacuum
- dissolutionThe residue is dissolved in 2 ml of dichloromethane
- filtrationfiltered through a short plug of silica gel (eluent: hexane/ethyl acetate 1/1 (v/v) to 0/100 (v/v))
Sources & evidence
- ORD record
- ord-167c5c9f9f214ff29d6e8950cbd0a1fc
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273890B2
Reaction notes
Loading…