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

HRID 2391683Notes

Reaction equation

HRID 2391683 reaction equation
[Si](OCC1N=CC2N(C3SC(C(OC)=O)=C(O)C=3)C=NC=2C=1)(C(C)(C)C)(C)C.[Si:29]([O:36][CH2:37][C:38]1[N:43]=[CH:42][C:41]2[N:44]=[CH:45][N:46]([C:47]3[S:51][C:50]([C:52]([O:54][CH3:55])=[O:53])=[C:49]([OH:56])[CH:48]=3)[C:40]=2[CH:39]=1)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30].C([O-])([O-])=O.[K+].[K+].Br[CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][C:66]=1[C:71]([F:74])([F:73])[F:72]>CN(C)C=O>[Si:29]([O:36][CH2:37][C:38]1[N:43]=[CH:42][C:41]2[N:44]=[CH:45][N:46]([C:47]3[S:51][C:50]([C:52]([O:54][CH3:55])=[O:53])=[C:49]([O:56][CH2:64][C:65]4[CH:70]=[CH:69][CH:68]=[CH:67][C:66]=4[C:71]([F:72])([F:73])[F:74])[CH:48]=3)[C:40]=2[CH:39]=1)([C:32]([CH3:33])([CH3:34])[CH3:35])([CH3:30])[CH3:31]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 68766004methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3H-imidazo[4,5-c]pyridin-3-yl]-3-hydroxythiophene-2-carboxylateHCID 68766707methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-hydroxythiophene-2-carboxylate

Product 1

HCID 68766097Methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-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, 2.08 g of an isomeric mixture of methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3H-imidazo[4,5-c]pyridin-3-yl]-3-hydroxythiophene-2-carboxylate and methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-hydroxythiophene-2-carboxylate (example C3) and 0.82 g of K2CO3 and 1.42 g of 1-(bromomethyl)-2-(trifluoromethyl)benzene in 15 ml N,N-dimethylformamide yield compound B2a and compound B2b.

Workup

  1. customyield compound B2a

Sources & evidence

ORD record
ord-437aa8611f7448f295b7a4d33439fed3
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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