Acetic Acid → 5-(3-Chloro-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline

HRID 539736ノート

反応式

HRID 539736 の反応式
[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([N+:20]([O-])=O)[CH:14]=1.CC(O)=O>C(O)C.O.[Fe]>[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([CH:14]=1)[NH2:20]

参加物

6

反応物 2

HCID 176Acetic AcidHCID 680891223-Chloro-6-methoxy-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazine

生成物 1

HCID 575162675-(3-Chloro-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline収率 89%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of 3-chloro-6-methoxy-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazine (0.25 g, 0.784 mmol) in ethanol (50 mL) and water (10 mL) containing AcOH (4.70 mmol) is added iron (0.218 g, 3.92 mmol). The reaction mixture is heated at 80° C. for 2 hours, cooled, concentrated under reduced pressure and sat. aqueous NaHCO3 (100 mL) is added. The mixture is extracted with EtOAc (3×50 mL). Organic layer is collected, dried over Na2SO4, filtered and concentrated to dryness. The crude product is purified via chromatography (hexanes to EtOAc) to afford the title compound (0.201 g, 89%) as a yellow solid: Rf 0.32 (EtOAc); LCMS (m/z)=289.4, 291.2 [M+H]+, tR=2.21 min.

後処理

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure and sat. aqueous NaHCO3 (100 mL)
  3. additionis added
  4. extractionThe mixture is extracted with EtOAc (3×50 mL)
  5. customOrganic layer is collected
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude product is purified via chromatography (hexanes to EtOAc)

出典と根拠

ORDレコード
ord-ea0b4462ee78402a8a736f7b50068a21
出典データセット
uspto-grants-2014_10
特許番号
US08871767B2

反応ノート

読み込み中…