Sodium Hydroxide → HCID 67229927, compound

HRID 1515746Notes

Reaction equation

HRID 1515746 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:19]([C:26]2[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][CH:27]=2)=[CH:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>C(O)C.O1CCCC1.C(OCC)(=O)C>[CH:21]1([CH:20]=[C:19]([C:26]2[CH:27]=[CH:28][C:29]([C:32](=[O:34])[CH3:33])=[CH:30][CH:31]=2)[C:11]2[NH:10][C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67227846HCID 67227846, compound

Product 1

HCID 67229927HCID 67229927, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-{4-[1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-ethanone (400 mg, 0.85 mmol) in ethanol (6 mL), tetrahydrofuran (4 mL) and an aqueous sodium hydroxide solution (10%, 1.5 mL) was heated at reflux for 48 h. The mixture was diluted with ethyl acetate (200 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 1-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-phenyl}-ethanone (250 mg, 89%) as a white solid: LC/MS m/e calcd for C22H22N2O [M+H]+ 331.43, observed 331.0.

Workup

  1. temperatureat reflux for 48 h
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-607cd644b6a14aa5986df756d9e49fd9
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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