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

HRID 2191699노트

반응식

HRID 2191699 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-19b302fce4034fc4b65c6e7619158580
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08327467B2

반응 노트

불러오는 중…