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

HRID 69212

반응식

HRID 69212 반응식
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

참가 물질

5

반응물 3

HCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 579172825,7-Difluoroquinoline-6-carbaldehyde2회HCID 178461629HCID 178461629, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-1835d5d588ce4b68a20bf0880f38cadb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822468B2

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