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

HRID 2391584Notes

Reaction equation

HRID 2391584 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+].[Cl:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[CH:52](Cl)[CH3:53]>CN(C)C=O>[Cl:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[CH:52]([O: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])[CH3:53].[Cl:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[CH:52]([O: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])[CH3:53]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 5870341-Chloro-2-(1-chloroethyl)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 68770215methyl 3-[1-(2-chlorophenyl)ethoxy]-5-(1H-imidazo[4,5-c]pyridin-1-yl)thiophene-2-carboxylateHCID 68771752methyl 3-[1-(2-chlorophenyl)ethoxy]-5-(3H-imidazo[4,5-c]pyridin-3-yl)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 206 mg 1-chloro-2-(1-chloroethyl)benzene in 5 ml N,N-dimethylformamide yield methyl 3-[1-(2-chlorophenyl)ethoxy]-5-(1H-imidazo[4,5-c]pyridin-1-yl)thiophene-2-carboxylate and methyl 3-[1-(2-chlorophenyl)ethoxy]-5-(3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate.

Sources & evidence

ORD record
ord-6cc1a026b5374f3e9d3757b5abf4d805
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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