1-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → HCID 76567863, compound

HRID 1728105Notes

Reaction equation

HRID 1728105 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6](/[C:7](=[CH:13]/[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)/[C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1.[F:21][C:22]1[CH:23]=[CH:24][C:25]([CH3:37])=[C:26]([CH:28]=[N:29][C:30]([O:32][Si](C)(C)C)=[CH2:31])[CH:27]=1>C1(C)C=CC=CC=1>[Cl:20][C:16]1[CH:15]=[C:14]([CH:13]2[CH2:31][C:30](=[O:32])[NH:29][CH:28]([C:26]3[CH:27]=[C:22]([F:21])[CH:23]=[CH:24][C:25]=3[CH3:37])[C:7]32[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[NH:9][C:8]3=[O:12])[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 701785041-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 131727338HCID 131727338, compound

Product 1

HCID 76567863HCID 76567863, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in example 1c, E/Z-6-methoxy-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole (0.4 g, 1.10 mmol) prepared in example 168b was reacted with 1-(5-fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene prepared in example 36a, in toluene to give racemic (2′R,3R,4′S)-4′-(3-chlorophenyl)-2′-(5-fluoro-2-methylphenyl)-6-methoxy spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.05 g, 10%).

Sources & evidence

ORD record
ord-ddb3b9a5878f4fa593eab0cb759f4558
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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