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

HRID 2174045ノート

反応式

HRID 2174045 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d1969f0c74b444ce9fe0f24b4e33138b
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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