Cesium carbonate → HCID 67239396、化合物

HRID 2363094ノート

反応式

HRID 2363094 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[S:20][C:21](Br)=[CH:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[CH:25]([C:28]1[CH:29]=[C:30]([OH:34])[CH:31]=[CH:32][CH:33]=1)([CH3:27])[CH3:26].C([O-])([O-])=O.[Cs+].[Cs+].CN1C(=O)CCC1>CCOC(C)=O.[Cu]I.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[S:20][C:21]([O:34][C:30]3[CH:31]=[CH:32][CH:33]=[C:28]([CH:25]([CH3:27])[CH3:26])[CH:29]=3)=[CH:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10]

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 120593-IsopropylphenolHCID 13387N-methyl-2-pyrrolidoneHCID 67238529HCID 67238529、化合物

生成物 1

HCID 67239396HCID 67239396、化合物収率 4.5%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In a 5 ml glass tube were placed 5-bromo-thiophene-2-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (50 mg, 0.14 mmol), 3-isopropylphenol (62 mg, 0.27 mmol), CuI (5 mg, weight of 10%), Cs2CO3 (88 mg, 0.27 mmol), NMP (1 mL), ethanol (1 mL), and a magnetic stir bar. The vial was sealed with septum and placed into the Microwave cavity. The vial was irradiated in a Microwave synthesizer at 195° C. for 120 min. The mixture was diluted with EtOAc and washed with 1N HCl and water. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane) to give title compound (2.5 mg, 4.5%).

後処理

  1. customIn a 5 ml glass tube were placed
  2. customThe vial was sealed with septum
  3. customThe vial was irradiated in a Microwave synthesizer at 195° C. for 120 min
  4. washwashed with 1N HCl and water
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane)

出典と根拠

ORDレコード
ord-41ec571d231a4a6ca469eed335b2b87c
出典データセット
uspto-grants-2014_04
特許番号
US08691855B2

反応ノート

読み込み中…