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

HRID 1518726ノート

反応式

HRID 1518726 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)[NH:4][C:3]=1[C:15](=[O:18])[CH2:16][CH3:17].C(O)C.[NH2:22][S:23]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)(=[O:25])=[O:24].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[NH:4][C:3]([C:15](=[O:18])[CH2:16][CH3:17])=[C:2]([C:29]3[CH:30]=[CH:31][C:26]([S:23]([NH2:22])(=[O:25])=[O:24])=[CH:27][CH:28]=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 682859721-(3-Bromo-5-(4-chlorophenyl)-4-methyl-1H-pyrrol-2-yl)propan-1-one2 回

生成物 1

HCID 601693534-(5-(4-chlorophenyl)-4-methyl-2-propionyl-1H-pyrrol-3-yl)benzene sulfonamide収率 6.7%

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 the solution of 1-(3-bromo-5-(4-chlorophenyl)-4-methyl-1H-pyrrol-2-yl)propan-1-one (compound 53b, 1.0 g, 3.06 mmol) in a mixture of toluene:ethanol (5:15 ml) was added 4-aminosulfonylbenzene boronic acid (0.67 g, 3.37 mmol) and potassium carbonate (1.26 g, 9.19 mmol) at a temperature of about 25° C. in a sealed tube and a nitrogen gas was bubbled through the resulting reaction mixture for 15 minutes. To the reaction mixture was then added tetrakis(triphenylphosphine)palladium(0) (0.17 g, 0.153 mmol) under nitrogen atmosphere and the reaction mixture was heated at about 90° C. to 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 (3×25 ml). The combined filtrate 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 (0.082 g, 6.65%).

後処理

  1. customa nitrogen gas was bubbled through the resulting reaction mixture for 15 minutes
  2. filtrationfiltered through celite
  3. washThe celite cake was washed with 10% methanol in dichloromethane (3×25 ml)
  4. concentrationThe combined filtrate was concentrated under reduced pressure
  5. customto obtain a crude product, which
  6. customwas then purified by flash column chromatography

出典と根拠

ORDレコード
ord-efc68d36739b4c7bbeb5fd2c5a4bbf4e
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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