1H-Indazol-5-amine → (6-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(1H-indazol-5-yl)-amine

HRID 746455Notes

Reaction equation

HRID 746455 reaction equation
[Br:1][C:2]1[N:3]=[C:4](Br)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[NH:12]1[C:20]2[C:15](=[CH:16][C:17]([NH2:21])=[CH:18][CH:19]=2)[CH:14]=[N:13]1>C(#N)C>[Br:1][C:2]1[N:3]=[C:4]([NH:21][C:17]2[CH:16]=[C:15]3[C:20](=[CH:19][CH:18]=2)[NH:12][N:13]=[CH:14]3)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 880121H-Indazol-5-amineHCID 150258436,8-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 57447601(6-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(1H-indazol-5-yl)-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.00 equivalent (eq.) of 6,8-dibromo-imidazo[1,2-a]pyrazine and 1.00 eq. of 1H-Indazol-5-ylamine are dissolved in acetonitrile and placed into a sealed tube and heated at 100° C. for 24 hours. The mixture is cooled to room temperature (RT) and partitioned between ethyl acetate (EtOAc) and saturated (sat.) NaHCO3. The aqueous phase is extracted with EtOAc and combined extracts are dried over Na2SO4. The solvent is removed under reduced pressure and the resulting residue is purified by flash chromatography (EtOAc) to yield (4).

Workup

  1. customplaced into a sealed tube
  2. temperatureThe mixture is cooled to room temperature (RT)
  3. custompartitioned between ethyl acetate (EtOAc) and saturated (sat.) NaHCO3
  4. extractionThe aqueous phase is extracted with EtOAc and combined extracts
  5. dry with materialare dried over Na2SO4
  6. customThe solvent is removed under reduced pressure
  7. customthe resulting residue is purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-b8c68c8344cf46af845a476308a42b3a
Source dataset
uspto-grants-2008_07
Patent number
US07393848B2

Reaction notes

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