Ethanol → 4-(5-(4-chlorophenyl)-1,4-dimethyl-2-propionyl-1H-pyrrol-3-yl)benzene sulfonamide

HRID 1053291Notes

Reaction equation

HRID 1053291 reaction equation
Br[C:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:4]([CH3:15])[C:3]=1[C:16](=[O:19])[CH2:17][CH3:18].C(O)C.[NH2:23][S:24]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)(=[O:26])=[O:25].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[N:4]([CH3:15])[C:3]([C:16](=[O:19])[CH2:17][CH3:18])=[C:2]([C:30]3[CH:31]=[CH:32][C:27]([S:24]([NH2:23])(=[O:26])=[O:25])=[CH:28][CH:29]=3)[C:6]=2[CH3:7])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 223919774-(Aminosulphonyl)benzeneboronic acidHCID 70912852HCID 70912852, compound2×

Product 1

HCID 601692574-(5-(4-chlorophenyl)-1,4-dimethyl-2-propionyl-1H-pyrrol-3-yl)benzene sulfonamideYield 33.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(3-bromo-5-(4-chlorophenyl)-1,4-dimethyl-1H-pyrrol-2-yl)propan-1-one (compound 49b, 3.0 g, 8.81 mmol) in a mixture of toluene:ethanol (15 ml:45 ml) were added 4-aminosulfonylbenzene boronic acid (1.947 g, 9.69 mmol) and potassium carbonate (2.43 g, 17.61 mmol) at 25° C. in a sealed tube and a nitrogen gas was bubbled through it for 15 minutes. To the reaction mixture was the added tetrakis(triphenylphosphine)palladium(0) (0.51 g, 0.44 mmol) under nitrogen atmosphere and reaction mixture was heated at about 90 to about 95° C. for 18 hr under stirring. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 25° C. and filtered through celite. The celite cake was washed with 10% methanol in dichloromethane. The combined filtrate so obtained was concentrated under reduced pressure to obtain a crude product, which was then purified by flash column chromatography using 40% ethyl acetate in hexanes as an eluent to obtain the title compound (1.22 g, 33.2%).

Workup

  1. customa nitrogen gas was bubbled through it for 15 minutes
  2. customreaction mixture
  3. temperaturewas heated at about 90 to about 95° C. for 18 hr
  4. filtrationfiltered through celite
  5. washThe celite cake was washed with 10% methanol in dichloromethane
  6. customThe combined filtrate so obtained
  7. concentrationwas concentrated under reduced pressure
  8. customto obtain a crude product, which
  9. customwas then purified by flash column chromatography

Sources & evidence

ORD record
ord-704c2be50431479296f516320e38e32c
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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