Bromine → Ethyl 3-bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine-6-carboxylate

HRID 229445Notes

Reaction equation

HRID 229445 reaction equation
[Br-:1].[K+].C([O-])(=O)C.[Na+].[CH2:8]([O:10][C:11]([C:13]1[C:14]([C:22]([F:25])([F:24])[F:23])=[N:15][C:16]2[N:17]([CH:19]=[CH:20][N:21]=2)[CH:18]=1)=[O:12])[CH3:9].BrBr.S(=O)(O)[O-].[Na+]>CO>[CH2:8]([O:10][C:11]([C:13]1[C:14]([C:22]([F:24])([F:25])[F:23])=[N:15][C:16]2[N:17]([C:19]([Br:1])=[CH:20][N:21]=2)[CH:18]=1)=[O:12])[CH3:9]

Participants

7

Reactant 5

HCID 24408BromineHCID 253877Potassium BromideHCID 517045Sodium AcetateHCID 23665763Sodium BisulfiteHCID 57758483Ethyl 7-(trifluoromethyl)imidazo[1,2-a]pyrimidine-6-carboxylate

Product 1

HCID 57758484Ethyl 3-bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium bromide (26.4 mg) and sodium acetate (2.5 eq, 6.6 mmol, 541 mg) were added sequentially to 7-trifluoromehyl-imidazo[1,2-a]pyrimidine-6-carboxylic acid ethyl ester (0.684 g, 2.64 mmol ) in methanol (5.5 mL) and the resulting mixture was stirred at room temperature for 30 minutes. The mixture was then cooled to −5° C. and bromine (1.02 eq, 0.138 mL) was added. Once addition was complete, the reaction was stirred for 1 hour. The mixture was then treated with a saturated aqueous solution of sodium bisulphite and, after stirring for 5 minutes, the solvents were removed under reduced pressure. Water was added to the residue and the pH adjusted with sodium hydroxide until just basic. The resulting solid was collected by filtration, washed with ether and crystallized from hot methanol to afford 3-bromo-7-trifluoromehyl-imidazo[1,2-a]pyrimidine-6-carboxylic acid ethyl ester in quantitative yield. m/z (M+H)=339.2.

Workup

  1. temperatureThe mixture was then cooled to −5° C.
  2. additionOnce addition
  3. stirringthe reaction was stirred for 1 hour
  4. stirringafter stirring for 5 minutes
  5. customthe solvents were removed under reduced pressure
  6. additionWater was added to the residue
  7. filtrationThe resulting solid was collected by filtration
  8. washwashed with ether
  9. customcrystallized from hot methanol

Sources & evidence

ORD record
ord-d0109c325c244af6a013d45637bffb37
Source dataset
uspto-grants-2009_07
Patent number
US07563797B2

Reaction notes

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