Ethanol → 2-{2-cyclopentyl-1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-vinyl}-1H-pyrrolo[2,3-b]pyridine

HRID 1515815Notes

Reaction equation

HRID 1515815 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]([S:32]([CH2:35][CH2:36][O:37][CH3:38])(=[O:34])=[O: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+].[CH2:41](O)C>O1CCCC1.ClCCl>[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:31]=[CH:30][C:29]([S:32]([CH2:35][CH2:36][O:37][CH2:38][CH3:41])(=[O:33])=[O:34])=[CH:28][CH:27]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 672295911-benzenesulfonyl-2-{2-cyclopentyl-1-[4-(2-methoxy-ethanesulfonyl)-phenyl]-vinyl}-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 672291462-{2-cyclopentyl-1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-vinyl}-1H-pyrrolo[2,3-b]pyridineYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-benzenesulfonyl-2-{2-cyclopentyl-1-[4-(2-methoxy-ethanesulfonyl)-phenyl]-vinyl}-1H-pyrrolo[2,3-b]pyridine (1.3 g, 2.36 mmol) in ethanol (10 mL), tetrahydrofuran (20 mL) and an aqueous sodium hydroxide solution (10%, 6 mL) was heated at 50° C. for 5 h. The mixture was diluted with dichloromethane (150 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 2-{2-cyclopentyl-1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-vinyl}-1H-pyrrolo[2,3-b]pyridine (900 mg, 90%): LC/MS m/e calcd for C24H28N2O3S [M+H]+ 425.57, observed 425.4.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification

Sources & evidence

ORD record
ord-99c898b056cd456e9063362a83492a88
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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