Ethyl Acetate → 3-Fluoro-4-(6-(pyridine-4-yl)-1H-indazole-5-yloxy)aniline

HRID 1661982ノート

反応式

HRID 1661982 の反応式
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)[NH:10][N:9]=[CH:8]2.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+].CCOC(C)=O>CCOC(C)=O.CCO>[F:1][C:2]1[CH:23]=[C:22]([CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)[NH:10][N:9]=[CH:8]2)[NH2:24]

参加物

6

反応物 4

HCID 8857Ethyl Acetate2 回HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 667667865-(2-fluoro-4-nitrophenoxy)-6-(pyridine-4-yl)-1H-indazole

生成物 1

HCID 667668543-Fluoro-4-(6-(pyridine-4-yl)-1H-indazole-5-yloxy)aniline収率 76.3%

試薬・触媒・溶媒 1

HCID 21584252Ethanol ethylacetate溶媒

反応条件

温度
80 °C

実験手順

A mixture of 5-(2-fluoro-4-nitrophenoxy)-6-(pyridine-4-yl)-1H-indazole (1.95 g, 4.5 mmol) and SnCl2.2H2O (10.2 g, 45.3 mmol) in EtOAc/EtOH (200 mL/10 mL) is stirred at 80° C. for 2 hours. Then aqueous NaHCO3 and EtOAc are added. The organic phase is dried over anhydrous MgSO4 and concentrated. The residue is purified by silica gel column chromatography eluting with PE:EtOAc (2:1) to give the desired product (1.10 g, 61.0% yield). MS (m/z): 321.0 (M+H).

後処理

  1. dry with materialThe organic phase is dried over anhydrous MgSO4
  2. concentrationconcentrated
  3. customThe residue is purified by silica gel column chromatography
  4. washeluting with PE

出典と根拠

ORDレコード
ord-48cc594eb1ef407f87b60aafbd8974bc
出典データセット
uspto-grants-2011_10
特許番号
US08030302B2

反応ノート

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