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

HRID 2391688Notes

Reaction equation

HRID 2391688 reaction equation
OC1C=C(N2C3C(=NC(OC)=CC=3)N=C2)SC=1C(OC)=O.[OH:22][C:23]1[CH:27]=[C:26]([N:28]2[C:32]3=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=[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]=[C:32]2[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)[CH:29]=[N:30][C:31]2=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 68764082methyl 3-hydroxy-5-(5-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)thiophene-2-carboxylateHCID 68770127methyl 3-hydroxy-5-(5-methoxy-1H-imidazo[4,5-b]pyridin-1-yl)thiophene-2-carboxylate

Product 1

HCID 68767171methyl 5-(5-methoxy-3H-imidazo[4,5-b]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, 1.4 g of an isomeric mixture of methyl 3-hydroxy-5-(5-methoxy-1H-imidazo[4,5-b]pyridin-1-yl)thiophene-2-carboxylate and methyl 3-hydroxy-5-(5-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)thiophene-2-carboxylate (example C9) and 0.76 g K2CO3 and 1.31 g 1-(bromomethyl)-2-(trifluoromethyl)benzene in 20 ml N,N-dimethylformamide yield compound B7a and compound B7b as crude material. These compounds were used for the next step (examples 22 and 23) without further purification.

Workup

  1. customyield compound B7a
  2. customThese compounds were used for the next step (examples 22 and 23) without further purification

Sources & evidence

ORD record
ord-668209a8751f4cb2b5d8bbccbdfc221c
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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