Ethyl4-(1-(3,4-Difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate → Ethyl2-tert-Butyl-3-(3,4-difluorobenzylcarbamoyl)-1H-indole-6-carboxylate

HRID 40114Notes

Reaction equation

HRID 40114 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:24](=O)[C:25]([CH3:28])([CH3:27])[CH3:26])[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=2)=[O:13])=[C:7]([N+:30]([O-])=O)[CH:6]=1)[CH3:2]>CO.[NH4+].[Cl-].[Zn]>[C:25]([C:24]1[NH:30][C:7]2[C:8]([C:11]=1[C:12](=[O:13])[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=1)=[CH:9][CH:10]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:33])[CH:6]=2)([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 1

HCID 59762433Ethyl4-(1-(3,4-Difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate2×

Product 1

HCID 59762341Ethyl2-tert-Butyl-3-(3,4-difluorobenzylcarbamoyl)-1H-indole-6-carboxylate

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

General Procedure R. To a solution of ethyl4-(1-(3,4-difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate (Compound 114, 91 mg, 0.20 mmol) in MeOH (10 ml) and saturated aqueous NH4Cl (5 ml) was added zinc dust (320 mg, 4.9 mmol). The mixture was stirred at room temperature for 0.5 h, filtered and concentrated. The remaining aqueous suspension was extracted with EtOAc (×3). The combined organic layer was 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.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. extractionThe remaining aqueous suspension was extracted with EtOAc (×3)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-e07e999b09bf429bae12abd21d92ba21
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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