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

HRID 597859ノート

反応式

HRID 597859 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c2bd167adc814fdfa0ba855d89d559f3
出典データセット
uspto-grants-2011_03
特許番号
US07897600B2

反応ノート

読み込み中…