Toluene → HCID 76567903, compound

HRID 1728169Notes

Reaction equation

HRID 1728169 reaction equation
C1(C)C=CC=CC=1.[F:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:24])=[C:13]([CH:15]=[N:16][C:17]([O:19][Si](C)(C)C)=[CH2:18])[CH:14]=1.C(OC([N:32]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([Cl:41])[CH:39]=2)/[C:34](=[CH:42]/[C:43]2[CH:48]=[C:47]([Cl:49])[CH:46]=[CH:45][C:44]=2[O:50][CH2:51][CH2:52][O:53]C(OC(C)(C)C)=O)/[C:33]1=[O:61])=O)(C)(C)C>CO>[Cl:41][C:38]1[CH:39]=[C:40]2[NH:32][C:33](=[O:61])[C:34]3([CH:42]([C:43]4[CH:48]=[C:47]([Cl:49])[CH:46]=[CH:45][C:44]=4[O:50][CH2:51][CH2:52][OH:53])[CH2:19][C:17](=[O:18])[NH:16][CH:15]3[C:13]3[CH:14]=[C:9]([F:8])[CH:10]=[CH:11][C:12]=3[CH3:24])[C:35]2=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 701785041-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86760819HCID 86760819, compound

Product 1

HCID 76567903HCID 76567903, compoundYield 1.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a toluene solution (10 mL) of 1-(5-fluoro-2-methyl-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (10.93 mmol) was added E/Z-3-[2-(2-tert-Butoxycarbonyloxy-ethoxy)-5-chloro-benzylidene]-6-chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (1 g, 1.82 mmol). Then the reaction tube was placed into the cavity of a focused monomode microwave reactor and the contents of the flask were irradiated at 130° C. for 40 min. After the solution was cooled to room temperature, methanol was added, and then the mixture was concentrated. Then a mixture of trifluoroacetic acid and dichloromethane was added. The reaction mixture was stirred at room temperature for 10 min. The solution was concentrated and the residue was purified by Prep-HPLC to give title compound as a white solid (11 mg).

Workup

  1. customThen the reaction tube was placed into the cavity of a focused monomode microwave reactor
  2. customthe contents of the flask were irradiated at 130° C. for 40 min
  3. concentrationthe mixture was concentrated
  4. additionThen a mixture of trifluoroacetic acid and dichloromethane
  5. additionwas added
  6. concentrationThe solution was concentrated
  7. customthe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-65af299ccb444bf7be3d78cf77f3a7d0
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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