Sodium Carbonate → Ethyl 2-(8,8-dimethyl-8H-indolo[3,2,1-de]acridin-3-yl)benzoate

HRID 1485591Notes

Reaction equation

HRID 1485591 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[N:8]3[C:21]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:15]([CH3:23])([CH3:22])[C:14]4[C:9]3=[C:10]([CH:11]=[CH:12][CH:13]=4)[C:4]=2[CH:3]=1.Cl[C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[C:27]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:22][C:15]1([CH3:23])[C:14]2[C:9]3=[C:10]([C:4]4[CH:3]=[C:2]([C:28]5[CH:29]=[CH:30][CH:25]=[CH:26][C:27]=5[C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:7]=[CH:6][C:5]=4[N:8]3[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=3)[CH:11]=[CH:12][CH:13]=2

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 230053604-Chloro-2-(ethoxycarbonyl)benzeneboronic acidHCID 671095853-Bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine

Product 1

HCID 71237009Ethyl 2-(8,8-dimethyl-8H-indolo[3,2,1-de]acridin-3-yl)benzoate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

39.8 g (110.0 mmol) of 3-bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine (Br-1), 30 g (110.0 mmol) of [4-chloro-2-(ethoxycarbonyl)phenyl]boronic acid and 9.7 g (92 mmol) of sodium carbonate are suspended in 350 ml of toluene, 350 ml of dioxane and 500 ml of water. 913 mg (3.0 mmol) of tri-otolylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene. The yield is 44 g (94 mmol), corresponding to 86% of theory.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. filtrationfiltered through silica gel
  6. washwashed three times with 200 ml of water
  7. customsubsequently evaporated to dryness
  8. customThe residue is recrystallised from toluene

Sources & evidence

ORD record
ord-0c890532de95416a90eee71809384e28
Source dataset
uspto-grants-2016_08
Patent number
US09422287B2

Reaction notes

Loading…