Chloroform ethylacetate → HCID 22388228, compound

HRID 1699903Notes

Reaction equation

HRID 1699903 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([CH:23]=[CH2:24])[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].C(Cl)(Cl)Cl.C(OCC)(=O)C>O1CCOCC1.[Pt](=O)=O>[Cl:1][C:2]1[CH:22]=[C:21]([CH2:23][CH3:24])[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

5

Reactant 2

HCID 21584013Chloroform ethylacetateHCID 22388184HCID 22388184, compound

Product 1

HCID 22388228HCID 22388228, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 3-(2-chloro-4-vinylbenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (230 mg, 0.67 mmol) in 1,4-dioxane (4.6 ml) was added platinum dioxide (23 mg) and the mixture was subjected to catalytic reduction at normal temperature. Six hours later, the reaction mixture was filtered through Celite and the filtrate was concentrated to give black crystals. The obtained crystals were subjected to flash silica gel chromatography (silica gel 40 ml, eluent: chloroform/ethyl acetate=5/1-4/1) and crystallized from diisopropyl ether to give the object compound (213 mg) as colorless crystals.

Workup

  1. filtrationSix hours later, the reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customto give black crystals
  4. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-9bfbe38b65cd4d678d90f786c856c411
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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