Sodium Hydroxide → HCID 57893482, compound

HRID 1821903Notes

Reaction equation

HRID 1821903 reaction equation
C1(S([N:10]2[C:14]3=[CH:15][N:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[CH:19]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[OH:20])(=O)=O)C=CC=CC=1.[OH-].[Na+]>C(O)C>[N:24]1[CH:25]=[CH:26][C:21]([C:19]([C:11]2[NH:10][C:14]3=[CH:15][N:16]=[CH:17][CH:18]=[C:13]3[CH:12]=2)=[O:20])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68983294HCID 68983294, compound

Product 1

HCID 57893482HCID 57893482, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[1-(Phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-2-yl](pyridin-4-yl)methanol (Reference Example 22, 217 mg, 0.59 mmol) was dissolved in ethanol (10 mL). A 10% solution of sodium hydroxide (6 mL) was added and the reaction mixture was refluxed for 4.5 hours and then stirred at ambient temperature for the weekend. 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 (pyridin-4-yl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (air-oxidation product) (86 mg, 65%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.26 (1H, s), 7.75-7.77 (1H, m), 7.90-7.92 (2H, m), 8.18 (1H, d, J=5.6 Hz), 8.81-8.83 (2H, m), 8.90 (1H, s); ESI MS m/z=224 [C13H9N3O+H]+; HPLC (Method A) >99% (AUC), tR=7.6 min.

Workup

  1. temperaturethe reaction mixture was refluxed for 4.5 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-cadeb5c28ff4406ab29e1332dc20706d
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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