Sodium Carbonate → HCID 22173111, compound

HRID 2298469Notes

Reaction equation

HRID 2298469 reaction equation
Cl[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:13]1(B(O)O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC1C=CC=CC=1C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:21]3[C:22]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:18]=[CH:19][CH:20]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2545321-Naphthaleneboronic acidHCID 117898227-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 22173111HCID 22173111, compoundYield 86.7%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalyst2×HCID 962WaterSolvent2×HCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

Using a method similar to Example 15b), 2.5 g (13.8 mmol) of 7-chloro-2-methyl-1-indanone (1), 2.97 g (17.3 mmol) of naphthylboronic acid and 3.66 g (34.6 mmol) of sodium carbonate were placed in 40 ml of o-xylene/5 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 1.55 mg (0.0069 mmol) of palladium acetate and 7.3 mg (0.027 mmol) of triphenylphosphine, the reaction mixture was stirred for 8 hours at 100° C. After 2, 4 and 6 hours, the same amount of palladium acetate and triphenyl phosphine were added again each time. After addition of 40 ml of water, the phases were separated, the aqueous phase was extracted 3 times with 40 ml each time of ether, the combined organic phases were washed with 40 ml of water and 40 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 3.26 g of (16) as solid.

Workup

  1. customthe mixture was degassed a number of times
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted 3 times with 40 ml each time of ether
  4. washthe combined organic phases were washed with 40 ml of water and 40 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-cdee70ff83f541ecb05be258e2af7f8f
Source dataset
uspto-grants-2002_12
Patent number
US06492539B1

Reaction notes

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