Benzyl 4-chlorosulfonyl-3-methoxybenzoate → Benzyl 4-[3-amino-5-chloro-3-(2-chlorophenyl)-2,3-dihydro-2-oxoindol-1-yl]sulfonyl-3-methoxybenzoate

HRID 234507Notes

Reaction equation

HRID 234507 reaction equation
[NH2:1][C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[NH:4][C:3]1=[O:12].Cl[S:21]([C:24]1[CH:39]=[CH:38][C:27]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])=[CH:26][C:25]=1[O:40][CH3:41])(=[O:23])=[O:22]>C(Cl)Cl.CCOC(C)=O>[NH2:1][C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]([S:21]([C:24]2[CH:39]=[CH:38][C:27]([C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])=[CH:26][C:25]=2[O:40][CH3:41])(=[O:23])=[O:22])[C:3]1=[O:12]

Participants

4

Reactant 2

HCID 15231551Benzyl 4-chlorosulfonyl-3-methoxybenzoateHCID 190763763-Amino-5-chloro-3-(2-chlorophenyl)-1,3-dihydroindol-2-one

Product 1

HCID 19076622Benzyl 4-[3-amino-5-chloro-3-(2-chlorophenyl)-2,3-dihydro-2-oxoindol-1-yl]sulfonyl-3-methoxybenzoateYield 78.7%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

This compound is prepared according to the procedure described in EXAMPLE 1 from 0.860 g of 3-amino-5-chloro-3-(2-chlorophenyl)-1,3-dihydroindol-2-one and 1 g of benzyl 4-chlorosulfonyl-3-methoxybenzoate. Chromatography on silica using a DCM/AcOEt mixture (99/1; v/v) as the eluent gives 1.38 g of the expected product, which is used as such in the next step.

Workup

  1. customThis compound is prepared

Sources & evidence

ORD record
ord-a97bad2ebba54401bf66eca606dc1748
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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