HCID 72323505, compound → HCID 72323504, compound

HRID 658939Notes

Reaction equation

HRID 658939 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)/[C:10](=[CH:18]/[C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=2[O:26][C:27]([C:30]([O:32][CH3:33])=[O:31])([CH3:29])[CH3:28])/[C:9]1=[O:34])=O)(C)(C)C.[F:35][C:36]1[C:41]([F:42])=[CH:40][C:39]([CH:43]=[N:44][C:45]([O:47][Si](C)(C)C)=[CH2:46])=[C:38]([CH3:52])[CH:37]=1>C1(C)C=CC=CC=1>[Cl:17][C:14]1[CH:15]=[C:16]2[NH:8][C:9](=[O:34])[C:10]3([CH:18]([C:19]4[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=4[O:26][C:27]([C:30]([O:32][CH3:33])=[O:31])([CH3:29])[CH3:28])[CH2:46][C:45](=[O:47])[NH:44][CH:43]3[C:39]3[CH:40]=[C:41]([F:42])[C:36]([F:35])=[CH:37][C:38]=3[CH3:52])[C:11]2=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 72323505HCID 72323505, compoundHCID 86632081HCID 86632081, compound

Product 1

HCID 72323504HCID 72323504, compoundYield 3.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of E/Z-6-chloro-3-[5-chloro-2-(1-methoxycarbonyl-1-methyl-ethoxy)-benzylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (1.5 g, 2.9 mmol) and 1-(4,5-difluoro-2-methyl-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (13 mmol) in toluene (13 mL) was heated at 60° C. for 3 h, and concentrated in vacuo. To the residue was added DCM (30 mL) and TFA (5 mL), and the resultant solution was stirred at room temperature for 3 h, then concentrated in vacuo. The residue was partitioned between ethyl acetate and aqueous diluted NaOH solution. The organic layer was washed with water to neutral, dried over anhydrous Na2SO4, and concentrated. The residue was purified by flash chromatography to give the title compound as white solid (60 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the residue was added DCM (30 mL) and TFA (5 mL)
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate and aqueous diluted NaOH solution
  5. washThe organic layer was washed with water to neutral,
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-bfd60cca93124d2899332fb1ab323783
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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