Bromine → HCID 22385760, compound

HRID 895145Notes

Reaction equation

HRID 895145 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[CH:7][N:6]2[CH:9]=[CH:10][N:11]=[C:5]2[CH:4]=1.C([O-])(=O)C.[Na+].[Br:19]Br>C(O)(=O)C>[Br:19][C:9]1[N:6]2[CH:7]=[N:8][C:3]([C:2]([F:12])([F:1])[F:13])=[CH:4][C:5]2=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 223857597-(Trifluoromethyl)imidazo[1,2-c]pyrimidine

Product 1

HCID 22385760HCID 22385760, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 7-trifluoromethylimidazo[1,2-c]pyrimidine (1.9239 g, 10.3 mmol) in acetic acid (40 ml) was added sodium acetate (1.265 g, 15.4 mmol), then a solution of bromine (0.529 ml, 10.3 mmol) in acetic acid (7.5 ml). The solution was stirred at room temperature for 30 min, then partitioned between saturated aqueous NaHCO3 (1 l) and ethyl acetate (500 ml). The aqueous layer (pH 8) was further extracted with ethyl acetate (500 ml), and the combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 20% EtOAc/isohexane) to afford 0.88 g (34% over 2 steps) of the title compound as a white solid: 1H NMR (360 MHz, CDCl3) δ 7.81 (1H, s), 7.93 (1H, s), 9.09 (1H, s).

Workup

  1. custompartitioned between saturated aqueous NaHCO3 (1 l) and ethyl acetate (500 ml)
  2. extractionThe aqueous layer (pH 8) was further extracted with ethyl acetate (500 ml)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (silica gel, 20% EtOAc/isohexane)

Sources & evidence

ORD record
ord-e902072ff3024f16b2a2416b57211e12
Source dataset
uspto-grants-2005_07
Patent number
US06914065B2

Reaction notes

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