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Toluene → 2-benzyl-6-chloro-4-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750237
Notes
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Reaction equation

HRID 750237 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1OS(C(F)(F)F)(=O)=O)=[CH:12][C:11]([Cl:23])=[CH:10][CH:9]=2)=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[F:38][C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1.C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C.O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:42]1[CH:43]=[CH:44][C:39]([F:38])=[CH:40][CH:41]=1)=[CH:12][C:11]([Cl:23])=[CH:10][CH:9]=2)=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 865995572-Benzyl-6-chloro-1-oxo-4-trifluoromethanesulfonyloxy-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester

Product 1

HCID 691568012-benzyl-6-chloro-4-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester
Yield 58.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-benzyl-6-chloro-1-oxo-4-trifluoromethanesulfonyloxy-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (100 mg), sodium carbonate (45 mg), 4-fluorophenylboronic acid (35 mg), tetrakis(triphenylphosphine)palladium(0) (12 mg), toluene (2.0 ml), water (0.4 ml) and ethanol (0.4 ml) in a pear shape flask with dimroth was deaerated in a vacuum line, substituted with argon and stirred at 80° C. for 12 hrs. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (52 mg) as a colorless powder.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-38b869a01649403d90cb58fd5b1bbf04
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07402595B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes