Lithium Hydroxide → HCID 59332629, compound

HRID 656053Notes

Reaction equation

HRID 656053 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-b5a0ff70cae449afb94ddf6dbf6f9c39
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

Loading…