Trifluoroacetic acid → 2-(2-chloro-6-methoxy-phenyl)-1H-indol-6-ylamine

HRID 1051228노트

반응식

HRID 1051228 반응식
C(OC(=O)[NH:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:17]3[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:25])[NH:14]2)=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:25][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH3:24])[C:17]=1[C:13]1[NH:14][C:15]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([NH2:7])[CH:16]=2

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 90102905[2-(2-chloro-6-methoxy-phenyl)-1H-indol-6-yl]-carbamic acid tert-butyl ester

생성물 1

HCID 742207322-(2-chloro-6-methoxy-phenyl)-1H-indol-6-ylamine수율 91.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of [2-(2-chloro-6-methoxy-phenyl)-1H-indol-6-yl]-carbamic acid tert-butyl ester (120 mg, 0.32 mmol) in CH2Cl2 (5 mL) was added 2,2,2-trifluoroacetic acid (0.5 mL) at 25° C. The solution was heated to reflux for 3 h, concentrated and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (70/30 hexanes/ethyl acetate) afforded 2-(2-chloro-6-methoxy-phenyl)-1H-indol-6-ylamine (80 mg, 91%) as a white solid. MH+ 272.9.

후처리

  1. temperatureThe solution was heated
  2. temperatureto reflux for 3 h
  3. concentrationconcentrated
  4. additionpoured into water
  5. extractionThe aqueous phase was extracted three times with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration
  9. concentrationfollowed by concentration in vacuo
  10. customgave a brown solid

출처 및 근거

ORD 기록
ord-31d88b4deee84ff89e3ea5126849925c
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388166B2

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