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

HRID 1518726노트

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HRID 1518726 반응식
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

참가 물질

7

반응물 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 223919774-(Aminosulphonyl)benzeneboronic acidHCID 682859721-(3-Bromo-5-(4-chlorophenyl)-4-methyl-1H-pyrrol-2-yl)propan-1-one2회

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
25 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-efc68d36739b4c7bbeb5fd2c5a4bbf4e
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09072731B2

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