Lithium Hydroxide → HCID 59332773, compound

HRID 387295Notes

Reaction equation

HRID 387295 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13]CC)=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][S:19](=[O:24])(=[O:23])[CH2:18]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[CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][S:19](=[O:23])(=[O:24])[CH2:18]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59332793HCID 59332793, compound

Product 1

HCID 59332773HCID 59332773, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 5-bromo-3-((1,1-dioxo-tetrahydro-2H-thiopyran-3-yl)methyl)-1H-indole-7-carboxylate (1.42 g, 0.034 mol) and LiOH (3.4 mL, 3 M) in MeOH (50 mL) was heated at reflux for one hour. The solvent was evaporated, and the mixture was acidified with 1N HCl and extracted with EtOAc (3×100 mL). The organic layer was dried, filtered and concentrated under reduced pressure, 1.30 (98.5%) of the title compound, which was carried on as is for the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one hour
  3. customThe solvent was evaporated
  4. extractionextracted with EtOAc (3×100 mL)
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure, 1.30 (98.5%) of the title compound, which
  8. customas is for the next step without further purification

Sources & evidence

ORD record
ord-f36a0f6013a84232a1b867c00aa6dd26
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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