Potassium Carbonate → methyl 5-(3H-imidazo[4,5-c]pyridin-3-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate

HRID 2391682Notes

Reaction equation

HRID 2391682 reaction equation
OC1C=C(N2C3C=CN=CC=3N=C2)SC=1C(OC)=O.[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[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[C:53]([F:56])([F:55])[F:54]>CN(C)C=O>[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][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[C:53]([F:54])([F:55])[F:56])[CH:25]=2)[CH:27]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 1230571-(Bromomethyl)-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 1

HCID 68766098methyl 5-(3H-imidazo[4,5-c]pyridin-3-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner as described for example B3, 7.92 g 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 4.77 g of K2CO3 and 8.23 g of 1-(bromomethyl)-2-(trifluoromethyl)benzene in 60 ml N,N-dimethylformamide yield compound B1a and compound B1b.

Workup

  1. customyield compound B1a

Sources & evidence

ORD record
ord-adf1de87494f4d8f92ac0b1ec7122dd0
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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