Water → 2-Methyl-7-(2-pyridyl)-1-indanone

HRID 2298479Notes

Reaction equation

HRID 2298479 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]2.C[Sn](C)(C)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.O>O1CCCC1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd]>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

Participants

6

Reactant 3

HCID 962WaterHCID 11021057Pyridine, 2-(trimethylstannyl)-HCID 158697837-Bromo-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 221730322-Methyl-7-(2-pyridyl)-1-indanoneYield 90%

Reagents, catalysts & solvents 2

HCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

16.9 g (75 mmol) of (2) and 20 g (90 mmol) of 2-trimethylstannylpyridine were placed in 165 ml of tetrahydrofuran in the reaction vessel, the mixture was degassed a number of times and saturated with argon. 350 mg (0.37 mmol) of trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium (II) were added and the reaction mixture was refluxed for 24 hours. After addition of 200 ml of water, the mixture was extracted 4 times with 150 ml each time of diethyl ether, the ether phase was washed with 100 ml of water and 100 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent and drying for 24 hours at 0.1 mbar at 60° C. (removal of the trimethylstannyl bromide) gave 15.07 g of (24) as an oil.

Workup

  1. customthe mixture was degassed a number of times
  2. temperaturethe reaction mixture was refluxed for 24 hours
  3. extractionthe mixture was extracted 4 times with 150 ml each time of diethyl ether
  4. washthe ether phase was washed with 100 ml of water and 100 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the solvent
  7. customdrying for 24 hours at 0.1 mbar at 60° C. (
  8. customremoval of the trimethylstannyl bromide)

Sources & evidence

ORD record
ord-8d66c37cfec241e5b6e56889f22a500b
Source dataset
uspto-grants-2002_12
Patent number
US06492539B1

Reaction notes

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