Dichloromethane → tert-Butyl 4-[[3-amino-3-(2-chlorophenyl)-5-ethoxy-2,3-dihydro-2-oxoindol-1-yl]methyl]benzoate

HRID 234549Notes

Reaction equation

HRID 234549 reaction equation
[NH2:1][C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH2:12][CH3:13])[CH:9]=2)[NH:4][C:3]1=[O:14].Br[CH2:23][C:24]1[CH:36]=[CH:35][C:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:26][CH:25]=1.C(Cl)Cl>CCCCCC.CCOC(C)=O>[NH2:1][C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH2:12][CH3:13])[CH:9]=2)[N:4]([CH2:23][C:24]2[CH:36]=[CH:35][C:27]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])=[CH:26][CH:25]=2)[C:3]1=[O:14]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11414578Tert-butyl 4-(bromomethyl)benzoateHCID 190763873-Amino-3-(2-chlorophenyl)-5-ethoxy-1,3-dihydroindol-2-one

Product 1

HCID 19076455tert-Butyl 4-[[3-amino-3-(2-chlorophenyl)-5-ethoxy-2,3-dihydro-2-oxoindol-1-yl]methyl]benzoateYield 64.7%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

This compound is prepared according to the procedure described in EXAMPLE 93 from 1 g of 3-amino-3-(2-chlorophenyl)-5-ethoxy-1,3-dihydroindol-2-one and 0.984 g of tert-butyl 4-bromomethylbenzoate. Chromatography on silica using DCM and then a DCM/AcOEt mixture (70/30; v/v) as the eluent gives 1.053 g of the expected product.

Workup

  1. customThis compound is prepared

Sources & evidence

ORD record
ord-87b3c295a0f14ff8bdbe6bc9ce903e65
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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