Ethanol → 1H-Pyrrolo(2,3-b)pyridine

HRID 1515741Notes

Reaction equation

HRID 1515741 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]2C(C2C=NC(OC)=CC=2)=CC2CCCC2)(=O)=O)C=CC=CC=1.C(O)C.O1CCCC1.[OH-].[Na+]>C(OCC)(=O)C>[NH:10]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[CH:12]=[CH:11]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 672287171-benzenesulfonyl-2-[2-cyclopentyl-1-(6-methoxy-pyridin-3-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 92221H-Pyrrolo(2,3-b)pyridineYield 253.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-benzenesulfonyl-2-[2-cyclopentyl-1-(6-methoxy-pyridin-3-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (110 mg, 0.24 mmol), ethanol (6 mL), tetrahydrofuran (3 mL) and an aqueous sodium hydroxide solution (10%, 1 mL) was heated at 40° C. for 4 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-(6-methoxy-pyridin-3-yl))-vinyl]-1H-pyrrolo[2,3-b]pyridine (72 mg, 94%) as a white solid: LC/MS m/e calcd for C20H21N3O [M+H]+ 320.41, observed 320.0.

Workup

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

Sources & evidence

ORD record
ord-dc19e8e1caff4589afd8055296dfa4bc
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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