Potassium Carbonate → 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole

HRID 1805965Notes

Reaction equation

HRID 1805965 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11]3[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH:23]1[C:31]2[C:30]3[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=3[S:28][C:27]=2[C:26](B(O)O)=[CH:25][CH:24]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C.C1(C)C=CC=CC=1>[CH:23]1[C:31]2[C:30]3[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=3[S:28][C:27]=2[C:26]([C:6]2[CH:5]=[C:4]([C:8]3[N:12]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:11]4[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=4[N:9]=3)[CH:3]=[CH:2][CH:7]=2)=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 2734329Dibenzothiophene-4-boronic acidHCID 230940652-(3-Bromophenyl)-1-phenyl-1H-benzoimidazole

Product 1

HCID 582402792-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

In a 50-mL three-neck flask were put 1.2 g (3.3 mmol) of 2-(3-bromophenyl)-1-phenyl-1H-benzimidazole, 0.8 g (3.3 mmol) of dibenzothiophen-4-boronic acid, and 50 mg (0.2 mmol) of tri(ortho-tolyl)phosphine. The air in the flask was replaced with nitrogen. To this mixture were added 3.3 mL of a 2.0 mmol/L aqueous solution of potassium carbonate, 12 mL of toluene, and 4 mL of ethanol. Under reduced pressure, this mixture was stirred to be degassed. Then, 7.4 mg (33 μmol) of palladium(II) acetate was added to this mixture, and the mixture was stirred at 80° C. for 6 hours under a nitrogen stream.

Workup

  1. customIn a 50-mL three-neck flask were put
  2. customto be degassed
  3. stirringthe mixture was stirred at 80° C. for 6 hours under a nitrogen stream

Sources & evidence

ORD record
ord-693d12c57b4744b586fa559c1572d750
Source dataset
uspto-grants-2013_01
Patent number
US08354542B2

Reaction notes

Loading…