Ammonium Chloride → 1-(3-(trifluoromethyl)benzyl)-1H-indazol-4-amine

HRID 706682ノート

反応式

HRID 706682 の反応式
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-])=O)[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[N:3]=1.[NH4+].[Cl-]>[Zn].CO>[F:24][C:21]([F:22])([F:23])[C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH2:14][N:4]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([NH2:11])[C:10]=2[CH:2]=[N:3]1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 679763573-iodo-4-nitro-1-(3-(trifluoromethyl)benzyl)-1H-indazole

生成物 1

HCID 679763551-(3-(trifluoromethyl)benzyl)-1H-indazol-4-amine収率 34%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

実験手順

To a round bottom flask was added 3-iodo-4-nitro-1-(3-(trifluoromethyl)benzyl)-1H-indazole (0.540 g, 1.21 mmol) and MeOH (12 mL). Zinc dust (0.395 g, 6.04 mmol) was added followed by saturated aqueous NH4Cl (12 mL). The mixture was stirred vigorously at ambient temperature for 2 hours. The reaction mixture was filtered and the solids were washed with EtOAc (30 mL). Saturated aqueous NH4OAc (25 mL) was added to the filtrate and the mixture was concentrated to remove organic solvents. The aqueous phase was then extracted with EtOAc (3×20 mL). The combined organic extracts were washed with a saturated aqueous NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated. The crude residue was purified by 1 mm preparative TLC using 5% MeOH/CH2Cl2 to afford 0.120 g (34%) of the product as a dark yellow/orange oil.

後処理

  1. filtrationThe reaction mixture was filtered
  2. washthe solids were washed with EtOAc (30 mL)
  3. additionSaturated aqueous NH4OAc (25 mL) was added to the filtrate
  4. concentrationthe mixture was concentrated
  5. customto remove organic solvents
  6. extractionThe aqueous phase was then extracted with EtOAc (3×20 mL)
  7. washThe combined organic extracts were washed with a saturated aqueous NaHCO3 solution and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude residue was purified by 1 mm preparative TLC

出典と根拠

ORDレコード
ord-5823ec072923445a8d3af5cebf1db7a0
出典データセット
uspto-grants-2015_11
特許番号
US09174981B2

反応ノート

読み込み中…