Methanol → 2-(oxazol-2-yl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine

HRID 1432210Notes

Reaction equation

HRID 1432210 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:23]2[O:24][CH:25]=[CH:26][N:27]=2)(=O)=O)C=CC=CC=1.[OH-].[K+].CO>O>[O:24]1[CH:25]=[CH:26][N:27]=[C:23]1[C:11]1[NH:10][C:14]2=[N:15][CH:16]=[C:17]([S:19]([CH3:22])(=[O:20])=[O:21])[CH:18]=[C:13]2[CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 225043901-benzenesulfonyl-2-(oxazol-2-yl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 225043982-(oxazol-2-yl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridineYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
22.5 °C

Procedure

A mixture of 1-benzenesulfonyl-2-(oxazol-2-yl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine (0.359 g), potassium hydroxide (0.34 g) and methanol (30 ml) was stirred at 15 to 30° C. for 30 minutes. To the reaction mixture was added water, the resulting mixture was extracted with dichloromethane, washed with a saturated aqueous NaCl solution, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate 1:1) to obtain 0.19 g of the desired product.

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane
  2. washwashed with a saturated aqueous NaCl solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2938dec03534478e8d94937c71cd4984
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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