(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(imidazo[1,2-a]pyridin-6-yl)methanone → (Rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(imidazo[1,2-a]pyridin-6-yl)ethanol

HRID 69291

反応式

HRID 69291 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([CH:19]=[CH:20][N:21]=4)[CH:18]=3)=[O:12])=[CH:9][N:10]=2)[N:7]=1.[CH3:22][Mg]Br>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([CH:19]=[CH:20][N:21]=4)[CH:18]=3)([OH:12])[CH3:22])=[CH:9][N:10]=2)[N:7]=1

参加物

4

反応物 2

HCID 87523683(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(imidazo[1,2-a]pyridin-6-yl)methanoneHCID 178418573HCID 178418573、化合物

生成物 1

HCID 87523871(Rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(imidazo[1,2-a]pyridin-6-yl)ethanol

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-imidazo[1,2-a]pyridin-6-yl-methanone (Stage 292.2, 4.0 g, 13.44 mmol) was suspended in dioxane (400 mL) and it was heated at 90° C. When all the material was in solution, it was cooled down to 50° C. and the 3 M methylmagnesium bromide solution (28.8 mL, 40.3 mmol) was added. It was refluxed for 2 h. Then it was cooled down to rt and the precipitate formed was filtered off. It was taken up with EtOAc/MeOH (9:1) and washed with saturated NaHCO3 solution and brine. The organic layer was dried over Na2SO4, filtered and concentrated to give the title compound as a brown solid (tR 0.3 min (conditions 2), MH+=314)

後処理

  1. temperaturewas cooled down to 50° C.
  2. temperatureIt was refluxed for 2 h
  3. temperatureThen it was cooled down to rt
  4. customthe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with saturated NaHCO3 solution and brine
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-f7c60afc4a2e46c5865e8ee3d2a3be15
出典データセット
uspto-grants-2014_09
特許番号
US08822468B2

関連ノート

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