HCID 86673034, compound → HCID 86673033, compound

HRID 1853265Notes

Reaction equation

HRID 1853265 reaction equation
[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]#[C:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:15]=2)[O:10][C:9]([C:25]2[N:26]=[CH:27][C:28]3[C:33]([CH:34]=2)=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].O1CCCC1.CO>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:15]=2)[O:10][C:9]([C:25]2[N:26]=[CH:27][C:28]3[C:33]([CH:34]=2)=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 86673034HCID 86673034, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86673033HCID 86673033, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-isoquinolin-3-yl-7-phenylethynyl-chromen-4-one O-tert-butyl oxime (60 mg, 0.13 mmol) (prepared using the procedure described in example 20 starting from example 2B) and Lindlar's catalyst (22.5 mg) in tetrahydrofuran (9.2 ml) and methanol (1.8 ml) was stirred at room temperature under 1 atmosphere of hydrogen for 18 h. The catalyst was removed by filtration and the solvent evaporated under reduce pressure to yield the title compound in 60% yield.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-438d06483e4f42aabe7f95a5d652aeae
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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