Water → 2-Methyl-7-(4-dimethylaminophenyl)-1-indanone

HRID 2298481Notes

Reaction equation

HRID 2298481 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.[CH3:13][N:14]([CH3:24])[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(COC)OC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1C1C=CC=CC=1P(C1C=CC=CC=1C1C=CC=CC=1C)C1C=CC=CC=1C1C=CC=CC=1C>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:18]3[CH:19]=[CH:20][C:15]([N:14]([CH3:24])[CH3:13])=[CH:16][CH:17]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343444-(Dimethylamino)phenylboronic acidHCID 158697837-Bromo-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 158697842-Methyl-7-(4-dimethylaminophenyl)-1-indanoneYield 76.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 22172997Tris(o-tolylphenyl)phosphineCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Using a method similar to Example 22, 8.0 g (0.032 mol) of (2), 5.85 g (0.038 mol) of 4-dimethylaminophenylboronic acid and 7.4 g (0.07 mol) of sodium carbonate were placed in 122 ml of dimethoxyethane and 37 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. 142 mg (0.6 mmol) of palladium acetate and 385 mg (1.3 mmol) of tris(o-tolylphenyl)phosphine were added and the reaction mixture was stirred for 4 hours at 80° C. After addition of 150 ml of water, the mixture was extracted 4 times with 100 ml each time of diethyl ether, the ether phase was washed twice with 50 ml each time of water and dried over magnesium sulfate. Removal of the solvent and column filtration through neutral aluminum oxide (dichloromethane) gave 6.5 g of 2-methyl-7-(4-dimethylaminophenyl)-1-indanone as an oil.

Workup

  1. custom37 ml of water in the reaction vessel, the mixture was degassed a number of times
  2. extractionthe mixture was extracted 4 times with 100 ml each time of diethyl ether
  3. washthe ether phase was washed twice with 50 ml each time of water
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the solvent and column filtration through neutral aluminum oxide (dichloromethane)

Sources & evidence

ORD record
ord-4e822485e7e04e669202c02b0f11970a
Source dataset
uspto-grants-2002_12
Patent number
US06492539B1

Reaction notes

Loading…