Piperidine → Z-3-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzylidene}-6-chloro-1,3-dihydro-indol-2-one

HRID 1512030Notes

Reaction equation

HRID 1512030 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:12]([Si:16]([CH3:31])([CH3:30])[O:17][CH2:18][CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:22]=1[CH:23]=O)([CH3:15])([CH3:14])[CH3:13].N1CCCCC1>CO>[C:12]([Si:16]([CH3:31])([CH3:30])[O:17][CH2:18][CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:22]=1/[CH:23]=[C:6]1\[C:7](=[O:11])[NH:8][C:9]2[C:5]\1=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)([CH3:14])([CH3:13])[CH3:15]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 575659162-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzaldehyde

Product 1

HCID 68755124Z-3-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzylidene}-6-chloro-1,3-dihydro-indol-2-oneYield 92.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 1, 6-chlorooxindole (2.37 g, 12.7 mmol) was reacted with 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzaldehyde prepared in Example 18 (4 g, 12.7 mmol) and piperidine (1.25 mL, 12.7 mmol) in methanol to give E/Z-3-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzylidene}-6-chloro-1,3-dihydro-indol-2-one as a yellow solid (Yield 5.46 g, 92%).

Sources & evidence

ORD record
ord-6b9a7d41af3e439c93fd5becb3dfabbc
Source dataset
uspto-grants-2012_07
Patent number
US08217051B2

Reaction notes

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