2,2,2-Trifluoroethanol → 3-Bromo-N-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-8-amine

HRID 457015Notes

Reaction equation

HRID 457015 reaction equation
[Br:1][C:2]1[N:6]2[C:7](Br)=[CH:8][N:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.C(O)C(F)(F)F.C(N(C(C)C)CC)(C)C>C(Cl)Cl.O>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH:20][C:17]3[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=3)[C:5]2=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 7732P-AnisidineHCID 81531DiisopropylethylamineHCID 142075923,5-Dibromoimidazo[1,2-a]pyrazine2×

Product 1

HCID 210709103-Bromo-N-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-8-amineYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3,5-Dibromo-imidazo[1,2-a]pyrazine (intermediate D) (200 mg, 0.7 mmol) was added to a mixture of anisidine (445 mg, 5 eq.), trifluoroethanol (3.6 ml), DIPEA (diisopropylethylamine) (0.629 ml, 5 eq). The mixture was heated at 75–85° C. in sealed tube for 12 hr. The mixture was then cooled to room temperature, diluted with DCM and water. The organic layer was washed with 1N HCl, brine, dried and concentrated. The residue was purified on a silica gel column to give 56.6 mg (yield 50%) of the title compound as faint orange solid.

Workup

  1. temperatureThe mixture was heated at 75–85° C. in sealed tube for 12 hr
  2. washThe organic layer was washed with 1N HCl, brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-c8ab6d3f93384311bb046bc4370a3268
Source dataset
uspto-grants-2007_03
Patent number
US07186832B2

Reaction notes

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