Sodium Hydroxide → HCID 67227843, compound

HRID 1515751Notes

Reaction equation

HRID 1515751 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]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[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:11]2[NH:10][C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=2)[C:26]2[CH:27]=[C:28]([CH3:33])[CH:29]=[C:30]([CH3:32])[CH:31]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67229747HCID 67229747, compound

Product 1

HCID 67227843HCID 67227843, compoundYield 101.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-benzenesulfonyl-2-[2-cyclopentyl-1-(3,5-dimethyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (130 mg, 0.28 mmol) in ethanol (3 mL), tetrahydrofuran (3 mL), and aqueous sodium hydroxide solution (10%, 1 mL) was heated at reflux for 24 h. The mixture was diluted with ethyl acetate (100 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-[2-cyclopentyl-1-(3,5-dimethyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (90 mg, 99%) as a white solid: LC/MS m/e calcd for C22H24N2 [M+H]+ 317.45, observed 317.2.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ee290d7b88c48dfb3131aec4a0a98db
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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