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

HRID 706682노트

반응식

HRID 706682 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5823ec072923445a8d3af5cebf1db7a0
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174981B2

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