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Sodium Carbonate → 1,4-Dichloro-7-(4-methylphenyl)isoquinoline

HRID 1067233
Notes
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Reaction equation

HRID 1067233 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:13])=[CH:7][N:8]=[C:9]2[Cl:12])=[CH:4][CH:3]=1.[CH3:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.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>[Cl:12][C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([C:18]3[CH:19]=[CH:20][C:15]([CH3:14])=[CH:16][CH:17]=3)[CH:11]=2)[C:6]([Cl:13])=[CH:7][N:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 166583507-Bromo-1,4-dichloroisoquinoline

Product 1

HCID 211924321,4-Dichloro-7-(4-methylphenyl)isoquinolineYield 48%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst
HCID 80711,2-DimethoxyethaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-bromo-1,4-dichloroisoquinoline (276 mg, 1.0 mmol), tetrakis(triphenylphosphine)palladium(0) (60 mg, 5 mol %), 4-methyphenylboronic acid (137 mg, 1.00 mmol), and aqueous Na2CO3 (2.0 mL, 1.0 M, 2.0 mmol) in DME (6 mL) was heated at reflux under N2 for 20 h. The mixture was diluted with EtOAc (100 mL), washed with water (30 mL), dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography upon silica gel using hexanes-EtOAc (99:1 to 97:3) as eluant to give 1,4-dichloro-7-(4-methylphenyl)isoquinoline (139 mg, 0.48 mmol) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under N2 for 20 h
  3. washwashed with water (30 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography upon silica gel

Sources & evidence

ORD record
ord-bf69c2f7b1ff4f77b70daa801b68bf2e
Source dataset
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06248738B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes