HCID 13922465, compound → HCID 20228696, compound

HRID 1731361Notes

Reaction equation

HRID 1731361 reaction equation
[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]2=[N:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=O)[CH3:20])=[C:14]([N+:22]([O-])=O)[CH:13]=1.[H][H]>CO.[Pd]>[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]2=[N:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]2[N:18]=[C:19]([CH3:20])[NH:22][C:14]=2[CH:13]=1

Participants

5

Reactant 2

HCID 13922465HCID 13922465, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20228696HCID 20228696, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3,7-dimethyl-2-(4-acetoamido-3-nitrophenyl)imidazo[1,2-a]pyridine (2 g) in methanol (200 ml) was hydrogenated over 10% palladium on carbon (wet, 400 mg) under an atmospheric pressure of hydrogen at ambient temperature for 2 hours. The catalyst was filtered off and the filtrate was concentrated to 20 ml of volume and allowed to stand overnight. Th.e precipitates were filtered off and the filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography on aluminum oxide (50 g) eluting with chloroform. The fractions containing the object compound were combined and allowed to stand overnight. The resultant yellow needles were collected by filtration and dried under reduced pressure to afford 5-(3,7-dimethylimidazo[1,2-a]pyridin-2-yl)-2-methylbenzimidazole (0.51 g). mp. 250°-253° C. (dec.).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to 20 ml of volume
  3. filtrationTh.e precipitates were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. washeluting with chloroform
  6. additionThe fractions containing the object compound
  7. waitto stand overnight
  8. filtrationThe resultant yellow needles were collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-8927cfb9adde45f6a6f4a20df9e146f8
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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