Water → Methyl 3-bromo-8-chloroimidazo[1,2-A]pyrazine-2-carboxylate

HRID 513213Notes

Reaction equation

HRID 513213 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[N:10]=2)[CH:5]=[CH:6][N:7]=1.C1C(=O)N([Br:22])C(=O)C1.O>C(#N)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:22][C:8]1[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]2=[N:10][C:9]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 71743177Methyl 8-chloroimidazo[1,2-A]pyrazine-2-carboxylate

Product 1

HCID 71743174Methyl 3-bromo-8-chloroimidazo[1,2-A]pyrazine-2-carboxylateYield 80.9%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 8-chloroimidazo[1,2-a]pyrazine-2-carboxylate (9.9 g, 46.8 mmol) in acetonitrile (600 mL) was added NBS (8.9 g, 50.1 mmol), and benzoyl peroxide (90 mg, 0.37 mmol). The mixture was then heated to reflux for 1 h, cooled to r.t., and water (1800 mL) was added. The resulting solids were filtered, washed with water, and air dried to give the title compound (11 g). LRMS (ESI) calc (M+H)+=289.9/291.9. found 290.0/292.0

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 1 h
  3. filtrationThe resulting solids were filtered
  4. washwashed with water, and air
  5. customdried

Sources & evidence

ORD record
ord-93c14d7e5079469c91bdfeac51f3e372
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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