alpha-Bromo-o-chlorotoluene → 1-(2-chlorobenzyl)-7-methyl-1H-indole-2,3-dione

HRID 1297754Notes

Reaction equation

HRID 1297754 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2=[O:12].CCN(P1(N(C)CCCN1)=NC(C)(C)C)CC.[Cl:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33]Br>C(#N)C.C(Cl)Cl>[Cl:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[CH3:1])[C:7](=[O:12])[C:8]1=[O:11]

Participants

6

Reactant 3

HCID 11905alpha-Bromo-o-chlorotolueneHCID 143137-MethylisatinHCID 199900182-tert-butylimino-N,N-diethyl-1-methyl-1,3,2lambda5-diazaphosphinan-2-amine

Product 1

HCID 22147711-(2-chlorobenzyl)-7-methyl-1H-indole-2,3-dioneYield 88.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Combine 7-methylisatin (80 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) in acetonitrile (5 mL) in a 20 dram scintillation vial and shake on a rotator for 2.5 days at room temperature. Dilute with CH2Cl2 or acetonitrile and filter off beads. Concentrate in vacuo to obtain 126 mg (88%) of the title compound as crude product as a red-orange solid. MS (ES): m/z=286 (M+1).

Workup

  1. filtrationfilter off beads
  2. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-c35bb1d73e6e46a49c3249bb783d5cda
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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