Potassium Carbonate → HCID 68765381, compound

HRID 2391692Notes

Reaction equation

HRID 2391692 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Br.[OH:14][C:15]1[CH:19]=[C:18]([N:20]2[C:24]3[CH:25]=[N:26][CH:27]=[CH:28][C:23]=3[N:22]=[CH:21]2)[S:17][C:16]=1[C:29]([O:31][CH3:32])=[O:30].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:22]1[C:23]2[CH:28]=[CH:27][N:26]=[CH:25][C:24]=2[N:20]([C:18]2[S:17][C:16]([C:29]([O:31][CH3:32])=[O:30])=[C:15]([O:14][CH2:6][C:5]3[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=3[O:3][C:2]([F:13])([F:12])[F:1])[CH:19]=2)[CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27772542-(Trifluoromethoxy)benzyl bromideHCID 68765327methyl 3-hydroxy-5-(3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate

Product 1

HCID 68765381HCID 68765381, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

110 mg of 2-(trifluoromethoxy)benzyl bromide is added to a mixture of 100 mg of methyl 3-hydroxy-5-(3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate and 59.7 mg of potassium carbonate in 3 ml anhydrous DMF. The mixture is stirred for 14 h at room temperature. Ice water is added and the organic phase is extracted with dichloromethane. The organic phase is poured on a phase separator and the solvent is removed under vacuum. The residue is dissolved in ethyl acetate and filtered through a short plug of silica gel (eluent: ethyl acetate) to yield the title compound.

Workup

  1. extractionthe organic phase is extracted with dichloromethane
  2. additionThe organic phase is poured on a phase separator
  3. customthe solvent is removed under vacuum
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. filtrationfiltered through a short plug of silica gel (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-c835aded4fce46f9b2df00f5095dabf5
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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