Sodium Carbonate → HCID 67204585, compound

HRID 523040Notes

Reaction equation

HRID 523040 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([Br:14])[C:8]=3[S:7][C:6]=2[CH:15]=1.[C:16]1([N:22]2[C:34]3[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][C:29]=3[C:28]3[C:23]2=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:14][C:13]1[C:8]2[S:7][C:6]3[CH:15]=[C:2]([C:31]4[CH:32]=[CH:33][C:34]5[N:22]([C:16]6[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=6)[C:23]6[C:28]([C:29]=5[CH:30]=4)=[CH:27][CH:26]=[CH:25][CH:24]=6)[CH:3]=[CH:4][C:5]=3[C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 513584509-Phenyl-9H-carbazole-3-boronic acidHCID 67545459HCID 67545459, compound

Product 1

HCID 67204585HCID 67204585, compound

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

2.47 g (8.1 mmol) of tetrakistriphenylphosphinopalladium(0) are added to a vigorously stirred suspension of 6.8 g (20 mmol) of 3,6-dibromodibenzothiophene, 15 g (40 mmol) of 9-phenyl-9H-carbazole-3-boronic acid and 63.9 g (127 mmol) of Na2CO3 in 500 ml of DMF, and the mixture is subsequently heated under reflux for 16 h. After cooling, the precipitated solid is filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol and recrystallised three times from DMF (about 15 ml/g). Yield 17.4 g (33 mmol), 86.0%, purity 99.9% (HPLC).

Workup

  1. temperaturethe mixture is subsequently heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid is filtered off with suction
  5. washwashed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol
  6. customrecrystallised three times from DMF (about 15 ml/g)

Sources & evidence

ORD record
ord-7e2f9e5bdb804252aafb4477ccce91da
Source dataset
uspto-grants-2016_05
Patent number
US09334260B2

Reaction notes

Loading…