Sodium Hydroxide → HCID 67228668, compound

HRID 1515760Notes

Reaction equation

HRID 1515760 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]2[C:19]([C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)=[CH:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>C(O)C.O1CCCC1.ClCCl>[CH3:36][S:33]([C:30]1[CH:29]=[CH:28][C:27]([C:19]([C:11]2[NH:10][C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=2)=[CH:20][CH:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[CH:32][CH:31]=1)(=[O:34])=[O:35]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67229499HCID 67229499, compound

Product 1

HCID 67228668HCID 67228668, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-benzenesulfonyl-2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-pyran-4-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (0.45 g, 8.6 mmol) in ethanol (8 mL), tetrahydrofuran (8 mL) and an aqueous sodium hydroxide solution (10%, 3 mL) was heated at 50° C. for 2 h. The mixture was diluted with dichloromethane (50 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-pyran-4-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (260 mg, 78%) which was used in the next step without further purification: LC/MS m/e calcd for C21H22N2O3S [M+H]+ 383.49, observed 383.4.

Workup

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

Sources & evidence

ORD record
ord-f9c94f635d7e44d18d08603c7e933f64
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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