Acetic Acid → 5-(3-(4-Fluorophenyl)-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline

HRID 539740노트

반응식

HRID 539740 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]3=[N:10][C:9]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([N+:26]([O-])=O)[CH:20]=2)=[CH:4][CH:3]=1.CC(O)=O>C(O)C.O.[Fe]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]3=[N:10][C:9]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([CH:20]=2)[NH2:26])=[CH:4][CH:3]=1

참가 물질

6

반응물 2

HCID 176Acetic AcidHCID 679858303-(4-Fluorophenyl)-6-methoxy-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazine

생성물 1

HCID 680890985-(3-(4-Fluorophenyl)-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline수율 942.3%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of 3-(4-fluorophenyl)-6-methoxy-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazine (0.075 g, 0.0198 mmol) in ethanol (6 mL) and water (2 mL) containing AcOH (1.18 mmol) is added iron (0.055 g, 0.991 mmol). The reaction mixture is heated at 80° C. for 2 hours, cooled, concentrated under reduced pressure and sat. aqueous NaHCO3 (50 mL) is added. The mixture is extracted with EtOAc (3×20 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 0.065 g (95%) of the title compound as a yellow solid: Rf 0.36 (95:5 CH2Cl2:MeOH); LCMS (m/z)=349.4 [M+H]+, tR=2.31 min.

후처리

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure and sat. aqueous NaHCO3 (50 mL)
  3. additionis added
  4. extractionThe mixture is extracted with EtOAc (3×20 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-ab125acee47940fa99a8eeaf2311b3f9
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871767B2

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