Hydrochloric Acid → N-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}benzene-1,2-diamine

HRID 244402ノート

反応式

HRID 244402 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH:11]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[N:20]=[CH:19]2)[C:12]([F:15])([F:14])[F:13])([O-])=O.Cl.C(=O)(O)[O-].[Na+]>CO.[Zn]>[F:15][C:12]([F:13])([F:14])[CH:11]([NH:10][C:5]1[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[N:20]=[CH:19]2

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59437215(2-Nitrophenyl)-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}amine

生成物 1

HCID 24960191N-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}benzene-1,2-diamine収率 14%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

実験手順

To a solution of 100 mg (0.23 mmol) of (2-nitrophenyl)-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}amine in 10 mL of methanol was added 304 mg (4.65 mmol) of zinc powder followed by the addition of 4.65 mL (4.65 mmol) of 1 N aqueous HCl. After 1 hour, the mixture was made basic with saturated aqueous sodium bicarbonate and extracted with three 15 mL portions of ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by prep-TLC using 10-20% EtOAc/hexanes to provide 10 mg (14%) of the title compound as a white solid. MS m/z 401 (MH+).

後処理

  1. extractionextracted with three 15 mL portions of ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

出典と根拠

ORDレコード
ord-643e4eecb17d4f46ab63ae14627652fd
出典データセット
uspto-grants-2014_02
特許番号
US08658637B2

反応ノート

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