Chloroform ethylacetate → HCID 22388228, compound

HRID 1072883Notes

Reaction equation

HRID 1072883 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-2357ad2d03a2453bbf13a3540934d316
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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