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

HRID 539812ノート

反応式

HRID 539812 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 19096565Water ethanol溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5d2165add3ab4294976a27be5919c0b0
出典データセット
uspto-grants-2014_10
特許番号
US08871767B2

反応ノート

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