3-Bromo-6-chloroimidazo(1,2-b)pyridazine → (6-Chloroimidazo[1,2-b]pyridazin-3-yl)(5,7-difluoroquinolin-6-yl)methanol

HRID 69212

反応式

HRID 69212 の反応式
Br[C:2]1[N:6]2[N:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.C([Mg])C.[F:15][C:16]1[C:25]([CH:26]=[O:27])=[C:24]([F:28])[CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[N:21]2>C1COCC1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([CH:26]([C:25]3[C:16]([F:15])=[C:17]4[C:22](=[CH:23][C:24]=3[F:28])[N:21]=[CH:20][CH:19]=[CH:18]4)[OH:27])=[CH:3][N:4]=2)[N:7]=1

参加物

5

反応物 3

HCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 579172825,7-Difluoroquinoline-6-carbaldehyde2 回HCID 178461629HCID 178461629、化合物

生成物 1

HCID 58147519(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(5,7-difluoroquinolin-6-yl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-Bromo-6-chloro-imidazo[1,2-b]pyridazine (4.40 g, 18.95 mmol) was suspended in THF (189 mL) and the ethylmagnesium solution (3 M, 6.32 mL) was added slowly under nitrogen condition. The RM was stirred at rt for 15 min and the solution of 5,7-difluoro-quinoline-6-carbaldehyde (Intermediate F, 3.66 g, 18.95 mmol) was added. After 30 min, the reaction was quenched with 10% ammonium chloride. The precipitate was filtered off and a first part of the title compound was obtained as a white solid. The filtrate was concentrated and was taken up with 10% NH4Cl. The precipitate was filtered off and was washed with EtOAc. A second part of the title compound was obtained as a brown solid (tR 0.8 min (conditions 2), MH+=347).

後処理

  1. waitAfter 30 min
  2. customthe reaction was quenched with 10% ammonium chloride
  3. filtrationThe precipitate was filtered off

出典と根拠

ORDレコード
ord-1835d5d588ce4b68a20bf0880f38cadb
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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