Acridan → HCID 11737718, compound

HRID 2188227Notes

Reaction equation

HRID 2188227 reaction equation
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[Na+].Br[C:22]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:29]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[CH3:29][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([CH3:28])[C:22]=1[N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

Participants

7

Reactant 3

HCID 7106AcridanHCID 684712-Bromo-m-xyleneHCID 23676156Sodium t-butoxide

Product 1

HCID 11737718HCID 11737718, compoundYield 66.2%

Reagents, catalysts & solvents 3

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A mixture containing 5.0 g of acridan (0.027 mol), 186 mg of Pd(OAc)2 (8.2×10−4 mol), 186 mg of tri-t-butylphosphine (8.2×10−4 mol), 3.97 g of sodium t-butoxide (0.041 mol), and 6.12 g of 1-bromo-2,6-dimethylbenzene (0.033 mol) in 70 mL of dry toluene was stirred under argon at room temperature for 16 h. Since TLC analysis still showed the presence of starting material, the reaction mixture was heated at 85° C. for 3 h. The reaction mixture was cooled, filtered and the precipitate was washed with diethyl ether. The filtrate was passed through a 2″ plug of celite and concentrated to a brown solid. The crude product was chromatographed on silica gel with 5%-20% CH2Cl2 in hexanes to afford 5.1 g (66.2%) of N-(2,6-dimethylphenyl)acridan.

Workup

  1. temperaturethe reaction mixture was heated at 85° C. for 3 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. washthe precipitate was washed with diethyl ether
  5. concentrationconcentrated to a brown solid
  6. customThe crude product was chromatographed on silica gel with 5%-20% CH2Cl2 in hexanes

Sources & evidence

ORD record
ord-eee49ad47b904480acddde3fac4ddd24
Source dataset
uspto-grants-2002_06
Patent number
US06410732B2

Reaction notes

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