2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrrolo[2,3-b]pyridine → HCID 67228059, compound

HRID 1515625Notes

Reaction equation

HRID 1515625 reaction equation
[CH:1]1([CH:6]=[C:7]([C:18]2[NH:34][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][CH:27]4[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[O:28]4)[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>[Pd].CO>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:34][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][CH:27]4[CH2:31][O:30][C:29]([CH3:32])([CH3:33])[O:28]4)[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 672286442-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrrolo[2,3-b]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 67228059HCID 67228059, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrrolo[2,3-b]pyridine (310 mg, 0.65 mmol) and 10% palladium on activated carbon (100 mg) in methanol (250 mL) was heated at 50° C. under 50 bar of hydrogen in a steel bomb pressure for 8 h. The mixture was cooled to room temperature. The catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrrolo[2,3-b]pyridine (270 mg, 86.8%) as a white solid: LC/MS m/e calcd for C27H34N2O4S [M+H]+ 483.65, observed 483.3.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cecc0070343d4b31abdbb3a6e2c35516
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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