Potassium Carbonate → 1-benzenesulfonyl-3-(3,4-dimethoxy-phenyl)-1H-indole

HRID 1820880Notes

Reaction equation

HRID 1820880 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](Br)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C1C=CC([P]([Pd]([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)=CC=1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:25]3[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[C:27]([O:28][CH3:29])[CH:26]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27347023,4-Dimethoxyphenylboronic acidHCID 27762153-Bromo-(1-phenylsulfonyl)indole

Product 1

HCID 578917491-benzenesulfonyl-3-(3,4-dimethoxy-phenyl)-1H-indole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

1-Benzenesulfonyl-3-bromoindole 20 (350 mg, 1.0 mmol) was dissolved in tetrahydrofuran (6 mL). Into the solution was added 3,4-dimethoxyphenyl boronic acid (379 mg, 2.1 mmol), tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.05 mmol) and 1 M potassium carbonate (3 mL). The reaction mixture was heated in a CEM Discover microwave instrument at 120° C. for 10 minutes. The reaction mixture was concentrated under reduced pressure and partioned between ethyl acetate and saturated sodium bicabonate. The organic portion was dried over anhydrous magnesium sulfate, and filtered. The filtrate was adsorbed onto silica gel and purified by flash chromatography (5%-50% ethyl acetate:hexanes) to provide the desired product, 19, (359 mg, 88%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dry with materialThe organic portion was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. custompurified by flash chromatography (5%-50% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-915151a8ef954ae7b85b773df75a1584
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

Loading…