Sodium Hydroxide → HCID 68714337, compound

HRID 1159788Notes

Reaction equation

HRID 1159788 reaction equation
[OH-].[Na+].FC1C=CC(S([N:13]2[C:21]3[C:16](=[C:17]([CH2:24][N:25]4[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]4)[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=3)[CH:15]=[CH:14]2)(=O)=O)=CC=1>CCO>[CH3:23][O:22][C:19]1[CH:20]=[C:21]2[C:16]([CH:15]=[CH:14][NH:13]2)=[C:17]([CH2:24][N:25]2[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:30]2)[CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68714951HCID 68714951, compound

Product 1

HCID 68714337HCID 68714337, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

40% W/w aq. NaOH (1 mL) was added to tert-butyl 4-({1-[(4-fluorophenyl)sulfonyl]-6-methoxy-1H-indol-4-yl}methyl)piperazine-1-carboxylate (626 mg, 1.12 mmol) in EtOH (10 mL). The reaction was refluxed for 1.5 h, allowed to attain rt. and extracted with DCM (2×50 mL) and water (40 mL). The organic layers were combined, dried and concentrated to give 450 mg crude product. Purification was performed by preparative HPLC/UV (System A, 30-65% MeCN, 0.1% NH4OAc). The residue was extracted with DCM and water and the organic layer was dried, filtered and concentrated to give the title compound (130 mg, 32%, from 1-[(4-fluorophenyl)sulfonyl]-6-methoxy-4-vinyl-1H-indole; prepared according to the method of Intermediate 33) as a light brown solid. MS (ESI+) for C19H27N3O3 m/z 346 (M+H)+.

Workup

  1. temperatureThe reaction was refluxed for 1.5 h
  2. customto attain rt
  3. extractionand extracted with DCM (2×50 mL) and water (40 mL)
  4. customdried
  5. concentrationconcentrated
  6. customto give 450 mg crude product
  7. customPurification
  8. extractionThe residue was extracted with DCM and water
  9. customthe organic layer was dried
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-5b1b6ddea4e649d996e09f8239c1dd19
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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