Tert-butyl 4-(bromomethyl)benzoate → tert-Butyl 4-[5-chloro-3-(2-chlorophenyl)-2,3-dihydro-3-dimethylamino-2-oxoindol-1-yl]methylbenzoate

HRID 965564Notes

Reaction equation

HRID 965564 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])[N:12]([CH3:14])[CH3:13].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>CCOC(C)=O.CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:23][C:24]1[CH:36]=[CH:35][C:27]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])=[CH:26][CH:25]=1)[C:6](=[O:11])[C:5]2([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])[N:12]([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 11414578Tert-butyl 4-(bromomethyl)benzoateHCID 190765485-Chloro-3-(2-chlorophenyl)-1,3-dihydro-3-dimethylaminoindol-2-one

Product 1

HCID 19076573tert-Butyl 4-[5-chloro-3-(2-chlorophenyl)-2,3-dihydro-3-dimethylamino-2-oxoindol-1-yl]methylbenzoate

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

This compound is prepared according to the procedure described in EXAMPLE 89 from 1.5 g of 5-chloro-3-(2-chlorophenyl)-1,3-dihydro-3-dimethylaminoindol-2-one and 1.40 g of tert-butyl 4-bromomethylbenzoate. Chromatography on silica using a gradient of an AcOEt/ hexane mixture (from 10/90; v/v to 20/80; v/v) as the eluent gives the expected product. m=1.5 g.

Workup

  1. customThis compound is prepared

Sources & evidence

ORD record
ord-168a2709c154413bb0051b94fce2ec41
Source dataset
uspto-grants-1998_06
Patent number
US05773612

Reaction notes

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