Sodium Hydroxide → HCID 67228905, compound

HRID 1515606Notes

Reaction equation

HRID 1515606 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH:19]4[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[O:20]4)[CH:18]=[C:13]3[CH:12]=[C:11]2[C:26]([C:33]2[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:35][CH:34]=2)=[CH:27][CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>C(O)C>[CH:28]1([CH:27]=[C:26]([C:11]2[NH:10][C:14]3=[N:15][CH:16]=[C:17]([CH:19]4[CH2:23][O:22][C:21]([CH3:24])([CH3:25])[O:20]4)[CH:18]=[C:13]3[CH:12]=2)[C:33]2[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:35][CH:34]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67228130HCID 67228130, compound

Product 1

HCID 67228905HCID 67228905, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-1H-pyrrolo[2,3-b]pyridine (510 mg, 0.85 mmol), a 10% aqueous sodium hydroxide solution (1 mL) and ethanol (8 mL) was heated at 100° C. for 1 h. The mixture was cooled to 25° C., extracted with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-1H-pyrrolo[2,3-b]pyridine (320 mg, 81%) as a light yellow oil which was used in the next step without purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6833b2f5802f40b88ccc19cc9ab3b196
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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