alpha-Bromo-o-fluorotoluene → 6-bromo-2-(2-fluorobenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750134Notes

Reaction equation

HRID 750134 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4].[F:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]Br.C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=2[F:23])[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4]

Participants

5

Reactant 3

HCID 67968alpha-Bromo-o-fluorotolueneHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 691573826-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

Product 1

HCID 691563726-bromo-2-(2-fluorobenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterYield 15.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (54 mg), 2-fluorobenzylbromide (34 mg) and 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine resin (2.2 mmol/g, 110 mg) were suspended in dimethylformamide (2 ml), and the suspension was shaken at room temperature for 15 hr. using a shaking machine. After filtration, the solvent was evaporated under reduced pressure, and the obtained residue was purified by preparative HPLC to give the title compound (11 mg, 15%).

Workup

  1. filtrationAfter filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customthe obtained residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2ab4fa83562545edb854bf8d82b1d26e
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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