1-((6-methylpyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole → 3-ethyl-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine

HRID 79299

반응식

HRID 79299 반응식
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([N+:18]([O-])=O)[CH:14]=[CH:15][CH:16]=3)[C:11]([CH:21]=[CH2:22])=[N:10]2)[CH:5]=[CH:4][CH:3]=1>CCO.C(Cl)Cl.[OH-].[Pd+2].[OH-]>[CH2:21]([C:11]1[C:12]2[C:13]([NH2:18])=[CH:14][CH:15]=[CH:16][C:17]=2[N:9]([CH2:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=2)[N:10]=1)[CH3:22]

참가 물질

4

반응물 1

HCID 672597031-((6-methylpyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole

생성물 1

HCID 672598043-ethyl-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine수율 87.8%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 21584144Dichloromethane ethanol용매

실험 절차

To 1-((6-methylpyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole (28.2 g, 95.8 mmol, Example 5, step C) in EtOH/DCM (300 mL/10 mL) was added palladium hydroxide (15 g, 20% wt). The reaction was purged with N2 and charged with hydrogen to 45 psi. The reaction was recharged during the reaction to 45 psi 4-5 times for the first 30 minutes. After 2 hours, the reaction was stopped, filtered through Celite, and the filter pad was washed with MeOH/DCM/Et3N (1 L, 10:1:1). The filtrate was concentrated and silica gel chromatography (EtOAc/hexanes 1:3) to provide the desired product (22.4 g).

후처리

  1. customThe reaction was purged with N2
  2. additioncharged with hydrogen to 45 psi
  3. customThe reaction was recharged during the reaction to 45 psi 4-5 times for the first 30 minutes
  4. filtrationfiltered through Celite
  5. washthe filter pad was washed with MeOH/DCM/Et3N (1 L, 10:1:1)
  6. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-a4f5e7c48c9143ab82cd155c46a4ec4b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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