Potassium Carbonate → 2-[4-(2,8-diphenyldibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole

HRID 1805966Notes

Reaction equation

HRID 1805966 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.[C:23]1([C:29]2[CH:47]=[C:46](B(O)O)[C:32]3[S:33][C:34]4[CH:39]=[CH:38][C:37]([C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)=[CH:36][C:35]=4[C:31]=3[CH:30]=2)[CH:28]=[CH:27][CH:26]=[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>[C:23]1([C:29]2[CH:47]=[C:46]([C:2]3[CH:7]=[CH:6][C:5]([C:8]4[N:12]([C:13]5[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=5)[C:11]5[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=5[N:9]=4)=[CH:4][CH:3]=3)[C:32]3[S:33][C:34]4[CH:39]=[CH:38][C:37]([C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)=[CH:36][C:35]=4[C:31]=3[CH:30]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 230940702-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazoleHCID 583096712,8-Diphenyldibenzothiophen-4-boronic acid

Product 1

HCID 583095502-[4-(2,8-diphenyldibenzothiophen-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 1.8 g (5.0 mmol) of 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole, 2.2 g (5.8 mmol) of 2,8-diphenyldibenzothiophen-4-boronic acid, and 76 mg (0.2 mmol) of tri(ortho-tolyl)phosphine. The air in the flask was replaced with nitrogen. To this mixture were added 5.8 mL of a 2.0 mmol/L aqueous solution of potassium carbonate, 19 mL of toluene, and 6 mL of ethanol. Under reduced pressure, this mixture was stirred to be degassed. Then, 11 mg (50 μmol) of palladium(II) acetate was added to this mixture, and the mixture was stirred at 80° C. for 4 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 4 hours under a nitrogen stream

Sources & evidence

ORD record
ord-3cb554bd555047f69196a35e2e61fae0
Source dataset
uspto-grants-2013_01
Patent number
US08354542B2

Reaction notes

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