Acetic Acid → 5-(6-Chloroimidazo[1,2-b]pyridazin-2-yl)-2-ethylaniline

HRID 539812노트

반응식

HRID 539812 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[C:13]([N+:19]([O-])=O)[CH:12]=3)[N:10]=2)[N:7]=1.CC(O)=O>C(O)C.O.[Fe]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[C:13]([CH:12]=3)[NH2:19])[N:10]=2)[N:7]=1

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 575162286-Chloro-2-(4-ethyl-3-nitrophenyl)imidazo[1,2-b]pyridazine

생성물 1

HCID 575162295-(6-Chloroimidazo[1,2-b]pyridazin-2-yl)-2-ethylaniline수율 89.3%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 19096565Water ethanol용매

반응 조건

온도
80 °C

실험 절차

Iron powder (4.61 g, 0.0825 mol) is added to a mixture of 6-chloro-2-(4-ethyl-3-nitrophenyl)imidazo[1,2-b]pyridazine (5.0 g, 0.0165 mol) in EtOH—H2O (150 mL, 4:1)containing AcOH (5.66 mL, 0.099 mol) at 80° C. The mixture is stirred at 80° C. for 4 hrs. The reaction mixture is cooled to room temp, filtered through celite, washed with EtOAc and concentrated. The oily residue is dissolved in EtOAc (200 mL) and washed twice with 100 mL Sat. NaHCO3. Compound is concentrated onto celite and purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound (4.02 g, 89%). LCMS m/z=273.3, 275.3 [M+H]+, tR=1.93 min.

후처리

  1. temperatureThe reaction mixture is cooled to room temp
  2. filtrationfiltered through celite
  3. washwashed with EtOAc
  4. concentrationconcentrated
  5. dissolutionThe oily residue is dissolved in EtOAc (200 mL)
  6. washwashed twice with 100 mL Sat. NaHCO3
  7. concentrationCompound is concentrated onto celite
  8. custompurified by silica gel chromatography (0-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-5d2165add3ab4294976a27be5919c0b0
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871767B2

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