Lithium Hydroxide → HCID 59332629, compound

HRID 387293Notes

Reaction equation

HRID 387293 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13]C)=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:15][CH:16]1[CH2:21][CH2:20][S:19](=[O:23])(=[O:22])[CH2:18][CH2:17]1.[Li+].[OH-]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:15][CH:16]1[CH2:17][CH2:18][S:19](=[O:22])(=[O:23])[CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59332614HCID 59332614, compound

Product 1

HCID 59332629HCID 59332629, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-bromo-3-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methyl]-1H-indole-7-carboxylate (1.3 g, 3.26 mmol) in MeOH (50 mL) was added a solution of 3 N LiOH (3.5 mL, 9.77 mmol). The mixture was stirred for 2 hours at reflux. The reaction was concentrated, and the residue was dissolved in 1N NaOH and extracted with DCM. The combined organic layers were dried (MgSO4) and concentrated, giving 1.2 g (96%) of the title compound.

Workup

  1. temperatureat reflux
  2. concentrationThe reaction was concentrated
  3. dissolutionthe residue was dissolved in 1N NaOH
  4. extractionextracted with DCM
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-895249cf53624a7e81fd74308a6a349c
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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