Sodium Hydroxide → HCID 59762356, compound

HRID 40145Notes

Reaction equation

HRID 40145 reaction equation
C([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([N+:16]([O-:18])=[O:17])=[C:12]([F:15])[CH:13]=2)[N:8]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]=1[CH:26]([CH3:28])[CH3:27])=[O:5])C.[OH-].[Na+]>CCO.CCOC(C)=O>[CH2:19]([N:8]1[C:9]2[C:14](=[CH:13][C:12]([F:15])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)[C:6]([C:4]([OH:5])=[O:3])=[C:7]1[CH:26]([CH3:28])[CH3:27])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59762346HCID 59762346, compound2×

Product 1

HCID 59762356HCID 59762356, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

General Procedure Z. To a solution of ethyl1-benzyl-5-fluoro-2-isopropyl-6-nitro-1H-indole-3-carboxylate (Compound 169, 546 mg, 1.54 mmol) in EtOH (10 ml) was added 5 M NaOH (3.1 ml, 15.5 mmol). The reaction was heated at 80° C. for 5 h, diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound as a brown solid.

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-b69f89d9b609410b9caa665553412561
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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