Sodium Hydroxide → HCID 67229073, compound

HRID 1515788Notes

Reaction equation

HRID 1515788 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:30]2[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=2)=[CH:20]\[CH:21]2[CH2:29][CH2:28][C:23]3([O:27][CH2:26][CH2:25][O:24]3)[CH2:22]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>C(O)C.O1CCCC1.ClCCl>[O:24]1[C:23]2([CH2:28][CH2:29][CH:21](/[CH:20]=[C:19](\[C:11]3[NH:10][C:14]4=[N:15][CH:16]=[CH:17][CH:18]=[C:13]4[CH:12]=3)/[C:30]3[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=3)[CH2:22]2)[O:27][CH2:26][CH2:25]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67228909HCID 67228909, compound

Product 1

HCID 67229073HCID 67229073, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (Z)-1-benzenesulfonyl-2-[2-(1,4-dioxa-spiro[4.4]non-7-yl)-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (800 mg, 1.42 mmol) in ethanol (24 mL), tetrahydrofuran (16 mL) and an aqueous sodium hydroxide solution (10%, 4 mL) was heated at 45° C. for 3 h. The mixture was diluted with dichloromethane (50 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford (Z)-2-[2-(1,4-dioxa-spiro[4.4]non-7-yl)-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (570 mg, 95%): LC/MS m/e calcd for C23H24FN2O4S [M+H]+ 425.52, observed 425.0.

Workup

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

Sources & evidence

ORD record
ord-ce189900339f4ec28046154390205bd1
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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