HCID 68428573, compound → HCID 68426410, compound

HRID 642257Notes

Reaction equation

HRID 642257 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[C:8]2[C:14]([CH2:15][CH:16]=[CH2:17])=[C:13]([CH2:18][CH:19]=[CH2:20])[N:12]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].[H][H]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:28][C:29](=[O:34])[C:30]([CH3:31])([CH3:32])[CH3:33])=[C:8]2[C:14]([CH2:15][CH2:16][CH3:17])=[C:13]([CH2:18][CH2:19][CH3:20])[N:12]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 68428573HCID 68428573, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68426410HCID 68426410, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,3-diallyl-1-benzyl-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (710 mg, 1.54 mmol), 10% Pd—C (100 mg) in EtOAc (20 mL) was stirred at 1 atm hydrogen atmosphere for two days at room temperature. Then the catalysts were filtered off through celite, the filtrate was concentrated to give an oil, the crude product (628 mg), which is pure and used directly in the next step. The title compound: ESI MS (m/z): 465 (M+H+).

Workup

  1. filtrationThen the catalysts were filtered off through celite
  2. concentrationthe filtrate was concentrated
  3. customto give an oil

Sources & evidence

ORD record
ord-a515b64fa94d4f2f87fb3511b8838a12
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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