Toluene → 1-(9,9-Dimethyl-9H-fluoren-2-yl)isoquinoline

HRID 2246024Notes

Reaction equation

HRID 2246024 reaction equation
[CH3:1][C:2]1([CH3:18])[C:14]2[CH:13]=[C:12](B(O)O)[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.Cl[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][N:21]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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>[CH3:1][C:2]1([CH3:18])[C:14]2[CH:13]=[C:12]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][N:21]=3)[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 140539Isoquinoline, 1-chloro-HCID 22348454(9,9-Dimethyl-9H-fluoren-2-yl)boronic acid

Product 1

HCID 178598831-(9,9-Dimethyl-9H-fluoren-2-yl)isoquinolineYield 54.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

In a 100 ml-three-necked flask, 2.91 g (12.2 mmole) of 9,9-dimethylfluorene-2-boronic acid, 2.00 g (12.2 mmole) of 1-chloroisoquinoline, 10 ml of toluene, 5 ml of ethanol and 10 ml of 2M-sodium carbonate aqueous solution were placed and stirred at room temperature under nitrogen stream, and 0.44 g (0.38 mmole) of tetrakis(triphenylphosphine)palladium (0) was added thereto. Thereafter, reflux under stirring was performed for 5 hours under nitrogen stream. After completion of the reaction, the reaction product was cooled and extracted by addition of cold water and toluene. The organic layer was washed with saline water and dried on magnesium sulfate, followed by removal of the solvent under a reduced pressure to provide dry solid. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=50/1) to obtain 2.13 g (yield=54.2%) of 1-(9,9-dimethylfluorene-2-yl)isoquinoline.

Workup

  1. additionwas added
  2. temperatureThereafter, reflux
  3. customAfter completion of the reaction
  4. temperaturethe reaction product was cooled
  5. extractionextracted by addition of cold water and toluene
  6. washThe organic layer was washed with saline water
  7. customdried on magnesium sulfate
  8. customfollowed by removal of the solvent under a reduced pressure
  9. customto provide
  10. customdry solid
  11. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=50/1)

Sources & evidence

ORD record
ord-b6e2c17c4696448c86969bd2cb8d7d49
Source dataset
uspto-grants-2010_03
Patent number
US07687155B2

Reaction notes

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