Potassium Carbonate → methyl 5-(1H-imidazo[4,5-c]pyridin-1-yl)-3-{1-[2-(trifluoro-methyl)phenyl]ethoxy}thiophene-2-carboxylate

HRID 2391580Notes

Reaction equation

HRID 2391580 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([N:7]2[C:15]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N:9]=[CH:8]2)[S:4][C:3]=1[C:16]([O:18][CH3:19])=[O:17].[OH:20][C:21]1[CH:25]=[C:24]([N:26]2[C:30]3[CH:31]=[N:32][CH:33]=[CH:34][C:29]=3[N:28]=[CH:27]2)[S:23][C:22]=1[C:35]([O:37][CH3:38])=[O:36].C([O-])([O-])=O.[K+].[K+].Br[CH:46]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[C:54]([F:57])([F:56])[F:55])[CH3:47]>CN(C)C=O>[N:7]1([C:5]2[S:4][C:3]([C:16]([O:18][CH3:19])=[O:17])=[C:2]([O:1][CH:46]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=3[C:54]([F:55])([F:56])[F:57])[CH3:47])[CH:6]=2)[C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:9]=[CH:8]1.[N:28]1[C:29]2[CH:34]=[CH:33][N:32]=[CH:31][C:30]=2[N:26]([C:24]2[S:23][C:22]([C:35]([O:37][CH3:38])=[O:36])=[C:21]([O:20][CH:46]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=3[C:54]([F:55])([F:56])[F:57])[CH3:47])[CH:25]=2)[CH:27]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27756211-(1-Bromoethyl)-2-(trifluoromethyl)benzeneHCID 68765327methyl 3-hydroxy-5-(3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylateHCID 68766294methyl 3-hydroxy-5-(1H-imidazo[4,5-c]pyridin-1-yl)thiophene-2-carboxylate

Product 2

HCID 68767622methyl 5-(1H-imidazo[4,5-c]pyridin-1-yl)-3-{1-[2-(trifluoro-methyl)phenyl]ethoxy}thiophene-2-carboxylateHCID 68771304methyl 5-(3H-imidazo[4,5-c]pyridin-3-yl)-3-{1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner as described for example B3, 300 mg of an isomeric mixture of methyl 3-hydroxy-5-(1H-imidazo[4,5-c]pyridin-1-yl)thiophene-2-carboxylate and methyl 3-hydroxy-5-(3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate (example C1) and 181 mg K2CO3 and 332 mg 1-(1-bromoethyl)-2-(trifluoromethyl)benzene in ml N,N-dimethylformamide yield methyl 5-(1H-imidazo[4,5-c]pyridin-1-yl)-3-{1-[2-(trifluoro-methyl)phenyl]ethoxy}thiophene-2-carboxylate and methyl 5-(3H-imidazo[4,5-c]pyridin-3-yl)-3-{1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxylate.

Sources & evidence

ORD record
ord-7a0adca2d55d4b0da4cf6eb85b3e088e
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

Loading…