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

HRID 1518723ノート

反応式

HRID 1518723 の反応式
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

参加物

7

反応物 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 223919774-(Aminosulphonyl)benzeneboronic acidHCID 70912852HCID 70912852、化合物2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
25 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ac3823de5c4b459390d7eac7d595fa20
出典データセット
uspto-grants-2015_07
特許番号
US09072731B2

反応ノート

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