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

HRID 1051228ノート

反応式

HRID 1051228 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-31d88b4deee84ff89e3ea5126849925c
出典データセット
uspto-grants-2016_07
特許番号
US09388166B2

反応ノート

読み込み中…