Sodium Hydroxide → 3-furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanol

HRID 1821905Notes

Reaction equation

HRID 1821905 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]([C:8]2[N:16](S(C3C=CC=CC=3)(=O)=O)[C:11]3=[CH:12][N:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[OH:7])=[CH:2]1.[OH-].[Na+]>C(O)C>[O:1]1[CH:5]=[CH:4][C:3]([CH:6]([C:8]2[NH:16][C:11]3=[CH:12][N:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[OH:7])=[CH:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 689805421h-Pyrrolo[2,3-c]pyridine-2-methanol,a-3-furanyl-1-(phenylsulfonyl)-

Product 1

HCID 689822523-furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanolYield 122.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Furyl[1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanol (186 mg, 0.51 mmol) was dissolved in ethanol (10 mL). A 10% solution of sodium hydroxide (6 mL) was added and the reaction mixture was refluxed for 3 hours. The solvent was removed under vacuum. The residue was taken up in ethyl acetate, washed with water and brine, dried over sodium sulfate and concentrated to give 3-furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanol (134 mg, quant.) as a yellow foam: 1H NMR (500 MHz, DMSO-d6) δ 5.87 (1H, d, J=4.7 Hz), 6.06 (1H, d, J=4.9 Hz), 6.29 (1H, s), 6.49 (1H, s), 7.42 (1H, d, J=5.4 Hz), 7.60 (2H, s), 8.03 (1H, d, J=5.4 Hz), 8.65 (1H, s), 11.49 (1H, s).

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. customThe solvent was removed under vacuum
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c226689ff449431c89e20ca12711482b
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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