Water → 7-Vinyl-3,4-dihydroisoquinolin-1(2H)-one

HRID 2233209Notes

Reaction equation

HRID 2233209 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[CH:13](B1OB(C=C)OB(C=C)O1)=[CH2:14].C([O-])([O-])=O.[K+].[K+].O>COCCOC.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>[CH:13]([C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1)=[CH2:14]

Participants

7

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 2734807TrivinylboroxinHCID 250673307-Bromo-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 574868957-Vinyl-3,4-dihydroisoquinolin-1(2H)-oneYield 88%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 7-bromo-3,4-dihydro-1(2H)-isoquinolinone (0.679 g, 3.004 mmol) and tetrakis(triphenylphosphine)palladium(0) (174 mg, 0.150 mmol) in 1,2-dimethoxyethane (30 ml) was stirred at room temperature for 0.5 h before addition of triethenylboroxin.pyridine complex (295 mg, 1.218 mmol), K2CO3 (415 mg, 3.004 mmol) and water (10 ml). The reaction was heated at reflux for 1.5 h before cooling to room temperature and addition of water (50 ml). The mixture was extracted with 10% methanol/dichloromethane (3×100 ml), the organic layers were dried with magnesium sulphate and evaporated. Chromatography on silica, eluting with 0-100% ethyl acetate/hexane, gave the product (456 mg, 88%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1.5 h
  3. extractionThe mixture was extracted with 10% methanol/dichloromethane (3×100 ml)
  4. dry with materialthe organic layers were dried with magnesium sulphate
  5. customevaporated
  6. washChromatography on silica, eluting with 0-100% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6d5dc9edec094ee7967422efcae31bda
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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