1-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → HCID 76568072, compound

HRID 1728237Notes

Reaction equation

HRID 1728237 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]([Br:25])[CH:22]=[CH:21][C:20]=2[O:26][CH2:27][C:28]([F:31])([F:30])[F:29])/[C:9]1=[O:32])=O)(C)(C)C.[F:33][C:34]1[CH:35]=[CH:36][C:37]([CH3:49])=[C:38]([CH:40]=[N:41][C:42]([O:44][Si](C)(C)C)=[CH2:43])[CH:39]=1>C1(C)C=CC=CC=1.ClCCl>[F:29][C:28]([F:31])([F:30])[C:27]([OH:44])=[O:26].[Br:25][C:23]1[CH:22]=[CH:21][C:20]([O:26][CH2:27][C:28]([F:30])([F:29])[F:31])=[C:19]([CH:18]2[CH2:43][C:42](=[O:44])[NH:41][CH:40]([C:38]3[CH:39]=[C:34]([F:33])[CH:35]=[CH:36][C:37]=3[CH3:49])[C:10]32[C:11]2[C:16](=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[NH:8][C:9]3=[O:32])[CH:24]=1

Participants

6

Reactant 2

HCID 701785041-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86617605HCID 86617605, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 76568072HCID 76568072, compoundYield 9.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

In a manner similar to the method described in Example 228d, E/Z-3-[5-bromo-2-(2,2,2-trifluoro-ethoxy)-benzylidene]-6-chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (1.06 g, 2 mmol) was reacted with 1-(5-fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (10 mmol) in toluene and then trifluoroacetic acid in dichloromethane to give title compound as a white solid (0.06 g).

Sources & evidence

ORD record
ord-ecfb93f66cd1474eb3a22558f66baea5
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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