Z-6-chloro-3-isobutylidene-1,3-dihydro-indol-2-one → 6-chloro-2'-(3-chlorophenyl)-4'-isopropyl spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1727951Notes

Reaction equation

HRID 1727951 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:12]/[CH:13]([CH3:15])[CH3:14])/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[N:24][C:25]([O:27][Si](C)(C)C)=[CH2:26])[CH:20]=[CH:21][CH:22]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]2[NH:8][C:7](=[O:11])[C:6]3([CH:12]([CH:13]([CH3:14])[CH3:15])[CH2:27][C:25](=[O:26])[NH:24][CH:23]3[C:19]3[CH:20]=[CH:21][CH:22]=[C:17]([Cl:16])[CH:18]=3)[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68614382Z-6-chloro-3-isobutylidene-1,3-dihydro-indol-2-oneHCID 68961886HCID 68961886, compound

Product 1

HCID 1317273056-chloro-2'-(3-chlorophenyl)-4'-isopropyl spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 56.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in example 1c, E/Z-6-chloro-3-isobutylidene-1,3-dihydro-indol-2-one (0.25 g, 1.1 mmol) was reacted with 1-(3-chlorophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (1.2 g, 4.7 mmol) prepared in example 1b, in toluene to give racemic (2′S,3S,4′R)-6-chloro-2′-(3-chlorophenyl)-4′-isopropylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.25 g, 56%).

Sources & evidence

ORD record
ord-c706ed3ccef24450b74822cd49adf07d
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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