4-Bromobenzenesulfonamide → 4-(2-(3-Azabicyclo[3.1.0]hexan-3-ylmethyl)-4-(4-chlorophenyl)thiazol-5-yl)benzenesulfonamide

HRID 1051899ノート

反応式

HRID 1051899 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[CH:17]12[CH2:22][CH:21]1[CH2:20][N:19]([CH2:23][C:24]1[S:25][CH:26]=[C:27]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[N:28]=1)[CH2:18]2>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(N(C)C)=O>[CH:21]12[CH2:22][CH:17]1[CH2:18][N:19]([CH2:23][C:24]1[S:25][C:26]([C:2]3[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=3)=[C:27]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[N:28]=1)[CH2:20]2

参加物

6

反応物 3

HCID 696964-BromobenzenesulfonamideHCID 517044Potassium AcetateHCID 89813117HCID 89813117、化合物2 回

生成物 1

HCID 717353984-(2-(3-Azabicyclo[3.1.0]hexan-3-ylmethyl)-4-(4-chlorophenyl)thiazol-5-yl)benzenesulfonamide収率 22%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
150 °C

実験手順

4-bromobenzenesulfonamide (0.37 g, 1.57 mmol) and potassium acetate (0.28 g, 2.87 mmol) were added to a solution of 2-(3-azabicyclo[3.1.0]hexan-3-ylmethyl)-4-(4-chlorophenyl)thiazole (Step-2 of compound 102, 0.42 g, 1.43 mmol) in a DMA (5 ml) in a tube at 25° C. Nitrogen gas was bubbled through the reaction mixture for 15 minutes. Palladium acetate (0.032 g, 0.14 mmol) was then added to the reaction mixture under nitrogen atmosphere and the tube was sealed. The reaction mixture was heated at 150° C. for 20 hrs 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 ethyl acetate (20 ml). The combined filtrate was concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography using 30% ethyl acetate in hexanes as an eluent to obtain the title compound (0.14 g, 21.4%). MS: m/z 446 (M+1).

後処理

  1. customNitrogen gas was bubbled through the reaction mixture for 15 minutes
  2. customthe tube was sealed
  3. temperatureThe reaction mixture was then cooled to 25° C.
  4. filtrationfiltered through celite
  5. washThe celite cake was washed with ethyl acetate (20 ml)
  6. concentrationThe combined filtrate was concentrated under reduced pressure
  7. customto obtain a crude product, which
  8. customwas then purified by column chromatography

出典と根拠

ORDレコード
ord-53a1ef27cef4423db3f70cb0fc59f3a3
出典データセット
uspto-grants-2016_07
特許番号
US09388196B2

反応ノート

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