1-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → HCID 72323498, compound

HRID 658946Notes

Reaction equation

HRID 658946 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])[C:22]([F:26])=[CH:21][C:20]=2[O:27][C:28]([C:31]([O:33][CH3:34])=[O:32])([CH3:30])[CH3:29])/[C:9]1=[O:35])=O)(C)(C)C.[F:36][C:37]1[CH:38]=[CH:39][C:40]([CH3:52])=[C:41]([CH:43]=[N:44][C:45]([O:47][Si](C)(C)C)=[CH2:46])[CH:42]=1>C1(C)C=CC=CC=1>[Cl:17][C:14]1[CH:15]=[C:16]2[NH:8][C:9](=[O:35])[C:10]3([CH:18]([C:19]4[CH:24]=[C:23]([Cl:25])[C:22]([F:26])=[CH:21][C:20]=4[O:27][C:28]([C:31]([O:33][CH3:34])=[O:32])([CH3:29])[CH3:30])[CH2:46][C:45](=[O:47])[NH:44][CH:43]3[C:41]3[CH:42]=[C:37]([F:36])[CH:38]=[CH:39][C:40]=3[CH3:52])[C:11]2=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 701785041-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86647011HCID 86647011, compound

Product 1

HCID 72323498HCID 72323498, compoundYield 3.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of, E/Z-6-chloro-3-[5-chloro-4-fluoro-2-(1-methoxycarbonyl-1-methyl-ethoxy)-benzylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (1.4 g, 2.6 mmol) and 1-(5-fluoro-2-methyl-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (13 mmol) prepared in Example 4 in toluene (13 mL) was heated at 60° C. for 3 h, and concentrated. 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. The residue was partitioned between ethyl acetate and diluted aqueous NaOH solution. The organic layer was separated, washed with water, 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
  2. additionTo the residue was added DCM (30 mL) and TFA (5 mL)
  3. concentrationconcentrated
  4. customThe residue was partitioned between ethyl acetate and diluted aqueous NaOH solution
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1ec522f116b64f81affd0dee4289501b
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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