Sodium Bicarbonate → Tert-butyl 4-(benzothiophene-3-carboxamido)-2-(4-fluoroanilino)benzoate

HRID 2191699ノート

反応式

HRID 2191699 の反応式
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:3]=1.[S:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[C:25]([C:32](Cl)=[O:33])=[CH:24]1.C(=O)([O-])O.[Na+]>ClCCl.C(N(CC)CC)C>[S:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[C:25]([C:32]([NH:1][C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:3]=2)=[O:33])=[CH:24]1

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 2776338Benzo(b)thiophene-3-carbonyl chlorideHCID 68958505Tert-butyl 4-amino-2-(4-fluoroanilino)benzoate

生成物 1

HCID 68959063Tert-butyl 4-(benzothiophene-3-carboxamido)-2-(4-fluoroanilino)benzoate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8471Triethylamine溶媒

実験手順

To dichloromethane 3.0 mL solution of tert-butyl 4-amino-2-(4-fluoroanilino)benzoate 40 mg were added triethylamine 0.064 mL, benzothiophene-3-carbonyl chloride 55 mg and dichloromethane 1.5 mL at room temperature, and it was stirred at same temperature for 2 hours. Aminomethylated-polystyrene 250 mg was added to the reaction mixture, and it was stirred at room temperature for 4 hours. Saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and insoluble matter was filtrated. The organic layer was separated and collected, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=4:1] to give tert-butyl 4-(benzothiophene-3-carboxamido)-2-(4-fluoroanilino)benzoate.

後処理

  1. stirringwas stirred at room temperature for 4 hours
  2. filtrationwas filtrated
  3. customThe organic layer was separated
  4. customcollected
  5. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-19b302fce4034fc4b65c6e7619158580
出典データセット
uspto-grants-2012_12
特許番号
US08327467B2

反応ノート

読み込み中…