Potassium Carbonate → (4-Chloro-2-fluorophenyl)(6-chloro-2-methyl-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-3-yl)methanone

HRID 597859노트

반응식

HRID 597859 반응식
[NH2:1][CH2:2][C:3]1[C:4]2[N:5]([C:10]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[F:23])=[O:15])=[C:11]([CH3:13])[N:12]=2)[N:6]=[C:7]([Cl:9])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH2:32][O:33][CH2:34][CH2:35]Br>O>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]([C:10]2[N:5]3[N:6]=[C:7]([Cl:9])[CH:8]=[C:3]([CH2:2][N:1]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[C:4]3=[N:12][C:11]=2[CH3:13])=[O:15])=[C:17]([F:23])[CH:18]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 86642486(8-(Aminomethyl)-6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)(4-chloro-2-fluorophenyl)methanone

생성물 1

HCID 56954584(4-Chloro-2-fluorophenyl)(6-chloro-2-methyl-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-3-yl)methanone수율 31%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

Combine (8-(aminomethyl)-6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)(4-chloro-2-fluorophenyl)methanone (1.15 g, 3.3 mmol), water (12 mL), potassium carbonate (495 mg, 1.1 equiv.), and 2-bromoethyl ether (0.47 mL, 1.1 equiv) in a 20 mL microwave reaction vessel. Seal with a crimp cap then heat in a microwave reactor at 120° C. for 20 min. Cool to RT and partition between EA and water. Wash EA layer with aqueous saturated sodium chloride, and dry over anhydrous magnesium sulfate. Filter and concentrate in vacuo. Purify on silica gel (4:1 hexane:EA→2:1 hexane:EA→1:1 hexane:EA) to give the title compound (0.43 g, 31%) as a light yellow foam. LCMS (4 min)=423.0, 425.0, M+1.

후처리

  1. customSeal with a crimp
  2. customcap
  3. temperatureCool to RT
  4. custompartition between EA and water
  5. dry with materialWash EA layer with aqueous saturated sodium chloride, and dry over anhydrous magnesium sulfate
  6. filtrationFilter
  7. concentrationconcentrate in vacuo
  8. customPurify on silica gel (4:1 hexane

출처 및 근거

ORD 기록
ord-c2bd167adc814fdfa0ba855d89d559f3
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897600B2

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