Trifluoroacetic acid → 5-Methyl-1-tosyl-1H-indol-4-amine

HRID 2174045노트

반응식

HRID 2174045 반응식
[CH3:1][C:2]1[C:3]([NH:21]C(=O)OC(C)(C)C)=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[CH:5]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:6]=[CH:5][C:4]=2[C:3]=1[NH2:21]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86701666tert-Butyl (5-methyl-1-tosyl-1H-indol-4-yl)carbamate

생성물 1

HCID 867016685-Methyl-1-tosyl-1H-indol-4-amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl (5-methyl-1-tosyl-1H-indol-4-yl)carbamate (10.5 g, 26.2 mmol) in DCM (197 mL) was added TFA (65.5 mL), and the mixture was stirred at room temperature. After 20 minutes the reaction was concentrated, dissolved in EtOAc, washed with sat. aq. NaHCO3, dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-70% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 301.1 (M+H).

후처리

  1. concentrationAfter 20 minutes the reaction was concentrated
  2. dissolutiondissolved in EtOAc
  3. washwashed with sat. aq. NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (0-70% EtOAc in heptanes)

출처 및 근거

ORD 기록
ord-d1969f0c74b444ce9fe0f24b4e33138b
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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