Water → 1-benzyl-3-iodo-4-nitro-1H-indazole

HRID 79255노트

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HRID 79255 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.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:20]([N:4]1[C:5]2[C:10](=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=2)[C:2]([I:1])=[N:3]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178526562HCID 178526562, 화합물

생성물 1

HCID 672598901-benzyl-3-iodo-4-nitro-1H-indazole수율 69.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
25 °C

실험 절차

3-Iodo-4-nitro-1H-indazole (0.50 g; 1.73 mmol) was dissolved with stirring in dimethylformamide (15 mL) under an atmosphere of nitrogen. Potassium carbonate (0.478 g; 3.46 mmol) was added followed by benzyl bromide (0.325 g; 1.90 mmol). The mixture was stirred for 16 hours at 25° C. The mixture was added to water (50 mL) and ethyl acetate (50 mL) with stirring. The mixture was transferred to a reparatory funnel and the phases were separated. The ethyl acetate phase was dried over sodium sulfate, filtered and concentrated under vacuum. The crude product was purified by silica gel chromatography, eluting with hexane/ethyl acetate (5:1). The fractions containing product were concentrated under vacuum to give the 1-benzyl-3-iodo-4-nitro-1H-indazole as a yellow oil (456 mg).

후처리

  1. stirringwith stirring
  2. customThe mixture was transferred to a reparatory funnel
  3. customthe phases were separated
  4. dry with materialThe ethyl acetate phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with hexane/ethyl acetate (5:1)
  9. additionThe fractions containing product
  10. concentrationwere concentrated under vacuum

출처 및 근거

ORD 기록
ord-543b47ddfb1240c2ac0b87c04449be9f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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