1-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → HCID 72323512, compound

HRID 658942Notes

Reaction equation

HRID 658942 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][CH3:28])/[C:9]1=[O:29])=O)(C)(C)C.[F:30][C:31]1[CH:32]=[CH:33][C:34]([CH3:46])=[C:35]([CH:37]=[N:38][C:39]([O:41][Si](C)(C)C)=[CH2:40])[CH:36]=1>C1(C)C=CC=CC=1>[Cl:17][C:14]1[CH:15]=[C:16]2[NH:8][C:9](=[O:29])[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][CH3:28])[CH2:40][C:39](=[O:41])[NH:38][CH:37]3[C:35]3[CH:36]=[C:31]([F:30])[CH:32]=[CH:33][C:34]=3[CH3:46])[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 86647009HCID 86647009, compound

Product 1

HCID 72323512HCID 72323512, compoundYield 1.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of E/Z-6-chloro-3-(5-chloro-4-fluoro-2-methoxy-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (3 g, 6.8 mmol) and 1-(5-fluoro-2-methyl-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (30 mmol) prepared in Example 4 in toluene (30 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. The residue was partitioned between ethyl acetate and aqueous diluted NaOH solution. The organic layer was 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 in vacuo
  2. additionTo the residue was added DCM (30 mL) and TFA (5 mL)
  3. concentrationconcentrated
  4. customThe residue was partitioned between ethyl acetate and aqueous diluted NaOH solution
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1ee56cc81a8744f8a551d8811b9d1a27
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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