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

反応式

HRID 79299 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 21584144Dichloromethane ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a4f5e7c48c9143ab82cd155c46a4ec4b
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

関連ノート

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