Aniline → HCID 9814499, compound

HRID 751584Notes

Reaction equation

HRID 751584 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[Br:23][C:24]1[N:25]=[C:26](Br)[C:27]2[N:28]([CH:30]=[CH:31][N:32]=2)[CH:29]=1.[NH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)C.O>[Br:23][C:24]1[N:25]=[C:26]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:27]2[N:28]([CH:30]=[CH:31][N:32]=2)[CH:29]=1

Participants

9

Reactant 4

HCID 6115AnilineHCID 80271Tri-o-tolylphosphineHCID 150258436,8-Dibromoimidazo[1,2-a]pyrazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 9814499HCID 9814499, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Tri-o-tolylphosphine (1.1 g) is added to a suspension of tris(dibenzylideneacetone)dipalladium (1.65 g) in degassed toluene (50 mL) and the mixture is stirred at room temperature for 15 minutes (min). 6,8-Dibromo-imidazo[1,2-a]pyrazine (5.0 g) is then added and the mixture is stirred at room temperature for 15 minutes more. Aniline (1.52 g) is added followed by potassium t-butoxide (2.84 g) and the mixture is stirred at room temperature for 72 hr. Water (150 mL) is added and the mixture is extracted with ethyl acetate (3×150 mL), the extracts are washed with water (1×100 mL) and brine (1×100 mL), dried over MgSO4, and evaporated in vacuo to afford a gum. Trituration with diethyl ether affords (6-bromo-imidazo[1,2-a]pyrazin-8-yl)-phenyl-amine (4) as a brown solid.

Workup

  1. stirringthe mixture is stirred at room temperature for 15 minutes more
  2. stirringthe mixture is stirred at room temperature for 72 hr
  3. extractionthe mixture is extracted with ethyl acetate (3×150 mL)
  4. washthe extracts are washed with water (1×100 mL) and brine (1×100 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customto afford a gum

Sources & evidence

ORD record
ord-a1dd305c455e4d6a9da1a35592a6783e
Source dataset
uspto-grants-2008_07
Patent number
US07405295B2

Reaction notes

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