1,4-Cyclohexadiene → 4-{8-Methylimidazo[1,2-a]pyridin-2-yl}aniline

HRID 8373

Reaction equation

HRID 8373 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]3[CH:19]=2)=[CH:6][CH:5]=1)([O-])=O.C1CC=CCC=1>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]3[CH:19]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 220156662-(4'-Nitrophenyl)-8-methylimidazo[1,2-a]pyridine

Product 1

HCID 27710774-{8-Methylimidazo[1,2-a]pyridin-2-yl}anilineYield 54.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the product of Step A (1.48 g) and 1,4-cyclohexadiene (6.2 mL) and palladium (10% wt on activated carbon) (1.4 g) in ethanol (100 mL) was stirred at reflux temperature for 2 hours and cooled to ambient temperature and stirred for 12 hours. The reaction mixture was filtered through a pad of celite and the celite pad rinsed with ethanol (100 mL) and methanol (100 mL). The filtrate was collected and evaporated to yield the title compound (710 mg).

Workup

  1. temperatureat reflux temperature for 2 hours
  2. stirringstirred for 12 hours
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. washthe celite pad rinsed with ethanol (100 mL) and methanol (100 mL)
  5. customThe filtrate was collected
  6. customevaporated

Sources & evidence

ORD record
ord-062f5d4b3c2849adbc8b1554248e2c83
Source dataset
uspto-grants-2006_08
Patent number
US07087757B2

Linked notes

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