1-(Bromomethyl)-3-(trifluoromethyl)benzene → 3-iodo-4-nitro-1-(3-(trifluoromethyl)benzyl)-1H-indazole

HRID 706681노트

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HRID 706681 반응식
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1.C(N=C(N(C)C)N(C)C)(C)(C)C>CC#N>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=2)[N:3]=1

참가 물질

5

반응물 3

HCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 178526562HCID 178526562, 화합물

생성물 1

HCID 679763573-iodo-4-nitro-1-(3-(trifluoromethyl)benzyl)-1H-indazole수율 85.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

To a slurry of 3-iodo-4-nitro-1H-indazole (0.410 g, 1.42 mmol) and CH3CN (7.0 mL) was added 1-(bromomethyl)-3-(trifluoromethyl)benzene (0.261 mL, 1.70 mmol) and the solution was cooled to 0° C. 2-tert-Butyl-1,1,3,3-tetramethylguanidine (0.372 mL, 1.84 mmol) was added and the mixture was gradually warmed to ambient temperature where it stirred for 2 hours. The mixture was concentrated and diluted with saturated aqueous NH4Cl (20 mL) and EtOAc (75 mL). The layers were mixed and separated and the organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was passed through a silica gel plug eluting with 20% EtOAc/hexane to provide 0.542 g (85%) of the product as dark yellow/orange oil.

후처리

  1. temperaturethe mixture was gradually warmed to ambient temperature where it
  2. concentrationThe mixture was concentrated
  3. additiondiluted with saturated aqueous NH4Cl (20 mL) and EtOAc (75 mL)
  4. additionThe layers were mixed
  5. customseparated
  6. washthe organic phase was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washeluting with 20% EtOAc/hexane

출처 및 근거

ORD 기록
ord-2cf1b510d7344e71b45a69e87c0f7f47
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174981B2

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