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

HRID 539736

반응식

HRID 539736 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ea0b4462ee78402a8a736f7b50068a21
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871767B2

연결된 노트

불러오는 중…