Potassium Carbonate → methyl 5-(6-methoxy-1H-imidazo[4,5-c]pyridin-1-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate

HRID 2391687Notes

Reaction equation

HRID 2391687 reaction equation
OC1C=C(N2C3C=NC(OC)=CC=3N=C2)SC=1C(OC)=O.[OH:22][C:23]1[CH:27]=[C:26]([N:28]2[C:36]3[CH:35]=[C:34]([O:37][CH3:38])[N:33]=[CH:32][C:31]=3[N:30]=[CH:29]2)[S:25][C:24]=1[C:39]([O:41][CH3:42])=[O:40].C([O-])([O-])=O.[K+].[K+].Br[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[C:57]([F:60])([F:59])[F:58]>CN(C)C=O>[CH3:38][O:37][C:34]1[N:33]=[CH:32][C:31]2[N:30]=[CH:29][N:28]([C:26]3[S:25][C:24]([C:39]([O:41][CH3:42])=[O:40])=[C:23]([O:22][CH2:50][C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=4[C:57]([F:58])([F:59])[F:60])[CH:27]=3)[C:36]=2[CH:35]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 68765328methyl 3-hydroxy-5-(6-methoxy-1H-imidazo[4,5-c]pyridin-1-yl)thiophene-2-carboxylateHCID 68768518methyl 3-hydroxy-5-(6-methoxy-3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate

Product 1

HCID 68766502methyl 5-(6-methoxy-1H-imidazo[4,5-c]pyridin-1-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.20 g of an isomeric mixture of methyl 3-hydroxy-5-(6-methoxy-3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate and methyl 3-hydroxy-5-(6-methoxy-1H-imidazo[4,5-c]pyridin-1-yl)thiophene-2-carboxylate (example C6) in 15 ml anhydrous N,N-dimethylformamide were added 0.65 g of K2CO3 and 1.12 g of 1-(bromomethyl)-2-(trifluoromethyl)benzene under a nitrogen atmosphere. The reaction mixture was stirred for 12 h at room temperature and poured into 400 ml of ice water. The resulting solid was filtered, washed with water and dried under vacuum to give the crude title compounds as an isomeric mixture. The isomeric mixture was used for the next steps (examples 16, 17 and 18) without further purification.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-149ffc5fa8d346b0b60beefcd4a30d70
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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