Dimethylformamide → HCID 86101374, compound

HRID 1914399Notes

Reaction equation

HRID 1914399 reaction equation
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[CH3:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN(C)C=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[CH:11]=[CH:10][C:9]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 79799Tolylboronic acidHCID 58050554HCID 58050554, compound

Product 1

HCID 86101374HCID 86101374, compoundYield 72.2%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixed solution of 3.5 g of 1-bromo-6-(4-chlorophenyl)pyrene, 1.6 g of 4-methylphenylboronic acid, 4.9 g of tripotassium phosphate, 0.75 g of tetrabutylammonium bromide, 52 mg of palladium acetate and 30 ml of dimethylformamide was heated and stirred under a nitrogen gas stream at 130° C. for 3 hours. The solution was cooled to room temperature and 100 ml of water was poured into the solution, followed by filtration. The resulting solid was dissolved in 100 ml of dichloromethane and then filtered through Celite. The filtrate was evaporated, and then the resulting solid was washed with 30 ml of ethyl acetate and vacuum-dried to obtain 2.6 g of 1-(4-methylphenyl)-6-(4-chlorophenyl)pyrene. Next, a mixed solution of 2.6 g of 1-(4-methylphenyl)-6-(4-chlorophenyl)pyrene, 1.4 g of carbazole, 820 mg of sodium t-butoxide, 145 mg of tri-t-butylphosphine tetrafluoroborate, 320 mg of bis(dibenzylideneacetone)palladium and 50 ml of m-xylene was heated and stirred under a nitrogen gas stream at 140° C. for 6 hours. The solution was cooled to room temperature, filtered through Celite and then concentrated by evaporation. The resulting solid was purified by silica gel chromatography and then vacuum-dried to obtain 2.3 g of a white solid. 1H-NMR analytical results of the resulting powder are as follows and reveal that the resulting white solid is compound [29].

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfollowed by filtration
  3. dissolutionThe resulting solid was dissolved in 100 ml of dichloromethane
  4. filtrationfiltered through Celite
  5. customThe filtrate was evaporated
  6. washthe resulting solid was washed with 30 ml of ethyl acetate
  7. customvacuum-dried

Sources & evidence

ORD record
ord-59b6c0db58f4490f856f4ed247c79fec
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

Loading…