Methanol → HCID 69156040, compound

HRID 750158Notes

Reaction equation

HRID 750158 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]3[O:31][CH2:30][CH2:29][C:28]=3[CH:32]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:4].CO.[H][H]>[C].[Pd].C1COCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]3[O:31][CH2:30][CH2:29][C:28]=3[CH:32]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 10174312HCID 10174312, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69156040HCID 69156040, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-bromo-2-(2,3-dihydrobenzofuran-5-ylmethyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (400 mg), 10% palladium carbon (150 mg), methanol (6 ml) and THF (6 ml) was stirred at room temperature under 1 atm hydrogen pressure for 12 hrs. Palladium carbon was filtered off, and the filtrate was concentrated. The obtained residue was crystallized from ethyl acetate-hexane to give the title compound (310 mg).

Workup

  1. filtrationPalladium carbon was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe obtained residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-c918e43a5504479dadfce88a91370e5d
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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