Potassium Carbonate → 6-Chloro-2-methanesulfonyl-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazole

HRID 1960148Notes

Reaction equation

HRID 1960148 reaction equation
[Cl:1][C:2]1[C:3](I)=[CH:4][C:5]2[N:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[NH:7][C:6]=2[CH:14]=1.C([O-])([O-])=O.[K+].[K+].[CH3:22][N:23]1[C:31]2[C:26](=[CH:27][C:28](B(O)O)=[CH:29][CH:30]=2)[CH:25]=[CH:24]1>C1(C)C=CC=CC=1.O.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[C:3]([C:28]2[CH:27]=[C:26]3[C:31](=[CH:30][CH:29]=2)[N:23]([CH3:22])[CH:24]=[CH:25]3)=[CH:4][C:5]2[N:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[NH:7][C:6]=2[CH:14]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 27598671-Methyl-1H-indole-5-boronic acidHCID 574814665-chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole

Product 1

HCID 674473556-Chloro-2-methanesulfonyl-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazole

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a microwave reactor vial was added 6-chloro-5-iodo-2-(methylsulfonyl)-1H-benzimidazole 16-5 (2 g, 5.6 mmol), PdCl2(dppf) (205 mg, 8.4 mmol), K2CO3 (2.32 g 17 mmol), 1-methyl-5-indoleboronic acid (1.47 g, 8.4 mmol) in 20 mL of toluene and 6 mL H2O. The reaction was run in a microwave reactor for 7 min at 130° C. The reaction mixture was diluted with EtOAc (150 mL) and washed three times with 150 mL portions of saturated aqueous ammonium chloride. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Then CH2Cl2 was added and the desired product precipitated out of the solution. The resulting solid was collected by vacuum filtration and washed with copious amounts of CH2Cl2 to yield the title compound 16-6 as a white solid.

Workup

  1. washwashed three times with 150 mL portions of saturated aqueous ammonium chloride
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionThen CH2Cl2 was added
  6. customthe desired product precipitated out of the solution
  7. filtrationThe resulting solid was collected by vacuum filtration
  8. washwashed with copious amounts of CH2Cl2

Sources & evidence

ORD record
ord-dceb649e0d9f448898576e092ecf3664
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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