HCID 22388190, compound → HCID 22388085, compound

HRID 1072919Notes

Reaction equation

HRID 1072919 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21](/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18]>CO.C(Cl)(Cl)Cl.[Pt](=O)=O>[Cl:1][C:2]1[CH:22]=[C:21]([CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18]

Participants

4

Reactant 1

HCID 22388190HCID 22388190, compound

Product 1

HCID 22388085HCID 22388085, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 21584188Chloroform methanolSolvent2×

Procedure

Methyl 3-(2-chloro-4-(E)-(2-phenylethenyl)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (2.37 g) was dissolved in methanol/chloroform=1/4 (24 ml), and platinum(IV) oxide (169 mg) was added. The mixture was stirred under a hydrogen atmosphere at normal pressure for 4 hours. Platinum(IV) oxide (169 mg) was added, and the mixture was further stirred under a hydrogen atmosphere at normal pressure for 6 hr. The reaction mixture was filtered through Celite and the filtrate was concentrated to dryness under reduced pressure. The obtained residue was subjected to silica gel column chromatography (eluent: ethyl acetate/chloroform=1/3). The fraction containing the objective compound was concentrated under reduced pressure to give the objective compound (1.92 g) as a white powder.

Workup

  1. additionwas added
  2. stirringthe mixture was further stirred under a hydrogen atmosphere at normal pressure for 6 hr
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated to dryness under reduced pressure
  5. additionThe fraction containing the objective compound
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-73d546b084a74963bfd2ba9e0abe77d5
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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