alpha-Bromo-o-chlorotoluene → 1-(2-Chloro-benzyl)-7-ethyl-1h-indole-2,3-dione

HRID 1297755Notes

Reaction equation

HRID 1297755 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9](=[O:12])[C:8]2=[O:13])[CH3:2].CCN(P1(N(C)CCCN1)=NC(C)(C)C)CC.[Cl:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34]Br>>[Cl:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34][N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:1][CH3:2])[C:8](=[O:13])[C:9]1=[O:12]

Participants

4

Reactant 3

HCID 11905alpha-Bromo-o-chlorotolueneHCID 2473657-ethyl-2,3-dihydro-1H-indole-2,3-dioneHCID 199900182-tert-butylimino-N,N-diethyl-1-methyl-1,3,2lambda5-diazaphosphinan-2-amine

Product 1

HCID 589147231-(2-Chloro-benzyl)-7-ethyl-1h-indole-2,3-dioneYield 85%

Procedure

Using a method similar to Preparation 15, with 7-ethylisatin (88 mg, 0.5 mmol), 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene beads(630-720 mg, 1.4-1.6 mmol, 2.2 mmol/g, Fluka) and 2-chlorobenzyl bromide (0.065 mL, 0.5 mmol) gives 121 mg (85%) of the title compound as crude material as a red-orange solid. MS (ES): m/z=300 (M+1).

Workup

  1. customsimilar to Preparation 15

Sources & evidence

ORD record
ord-72ef6f480ddb4fdd87c80d0992694c21
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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