Potassium Carbonate → dimethyl 2-bromo-1-(but-2-ynyl)-1H-imidazole-4,5-dicarboxylate

HRID 2113477Notes

Reaction equation

HRID 2113477 reaction equation
Br[CH2:2][C:3]#[C:4][CH3:5].[Br:6][C:7]1[NH:8][C:9]([C:16]([O:18][CH3:19])=[O:17])=[C:10]([C:12]([O:14][CH3:15])=[O:13])[N:11]=1.C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[Br:6][C:7]1[N:11]([CH2:2][C:3]#[C:4][CH3:5])[C:10]([C:12]([O:14][CH3:15])=[O:13])=[C:9]([C:16]([O:18][CH3:19])=[O:17])[N:8]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 27568621-Bromo-2-butyneHCID 21947693Dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate

Product 1

HCID 21947677dimethyl 2-bromo-1-(but-2-ynyl)-1H-imidazole-4,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.06 g 1-bromo-2-butyne are added dropwise to a mixture of 6.00 g of dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate and 3.80 g of potassium carbonate in 40 ml of dimethylformamide. The mixture is stirred for 12 h at ambient temperature and then added to an aqueous saturated solution of sodium thiosulphate. The organic phase is separated off and the aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulphate, the solvent is removed and the residue is chromatographed over silica gel (cyclohexane/ethyl acetate 4:1>1:1).

Workup

  1. customThe organic phase is separated off
  2. extractionthe aqueous phase is extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. customthe solvent is removed
  5. customthe residue is chromatographed over silica gel (cyclohexane/ethyl acetate 4:1>1:1)

Sources & evidence

ORD record
ord-0b3c97df53334c5eb4328ea70f511474
Source dataset
uspto-grants-2008_10
Patent number
US07432262B2

Reaction notes

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