HCID 131735836, compound → HCID 131735835, compound

HRID 2206123Notes

Reaction equation

HRID 2206123 reaction equation
[C:1]1([C:6]2[C:14]3[C:13]([C:15]#[N:16])=[CH:12][N:11]=[C:10]([O:17][CH3:18])[C:9]=3[N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1>CO.[Pd]>[CH:1]1([C:6]2[C:14]3[C:13]([C:15]#[N:16])=[CH:12][N:11]=[C:10]([O:17][CH3:18])[C:9]=3[N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:26])[CH3:25])[CH:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 131735836HCID 131735836, compound

Product 1

HCID 131735835HCID 131735835, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(cyclopent-1-en-1-yl)-7-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine-4-carbonitrile (690 mg) in methanol (5 mL) was added 10% palladium/carbon (100 mg). The reaction mixture was stirred overnight under hydrogen atmosphere (1 atm) at 50° C., and the insoluble substance was removed by filtration through Celite. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (519 mg).

Workup

  1. customthe insoluble substance was removed by filtration through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-405314bcd3f444dd8284b8864af6e98f
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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