Imidazo[1,2-a]pyridine-6-carbaldehyde → (Rac)-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-imidazo[1,2-a]pyridin-6-yl-methanol

HRID 69167

반응식

HRID 69167 반응식
C([Mg]Br)C.Br[C:6]1[N:10]2[N:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1.[N:16]1[CH:17]=[CH:18][N:19]2[CH:24]=[C:23]([CH:25]=[O:26])[CH:22]=[CH:21][C:20]=12>C1COCC1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]2[N:10]([C:6]([CH:25]([C:23]3[CH:22]=[CH:21][C:20]4[N:19]([CH:18]=[CH:17][N:16]=4)[CH:24]=3)[OH:26])=[CH:7][N:8]=2)[N:11]=1

참가 물질

5

반응물 3

HCID 7164582Imidazo[1,2-a]pyridine-6-carbaldehydeHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 87523529(Rac)-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-imidazo[1,2-a]pyridin-6-yl-methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Ethyl magnesium bromide (3 M in Et2O, 333 μL, 1 mmol) was added to a solution of 3-bromo-6-chloro-imidazo[1,2-b]pyridazine (116 mg, 0.5 mmol) in THF (5 mL) at rt . The RM was stirred for 30 min and imidazo[1,2-a]pyridine-6-carbaldehyde (154 mg, 2 mmol) in THF (3 mL) was added dropwise. After 1 h the RM was extracted with a solution of NH4Cl and EtOAc. The combined organic phases were dried over Na2SO4, concentrated under reduced pressure, and purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, Hexane/EtOAc=95:5->0:100) to afford the title compound as a yellowish crystalline compound (tR 2.72 min (conditions 3), MH+=300.2).

후처리

  1. extractionAfter 1 h the RM was extracted with a solution of NH4Cl and EtOAc
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. custompurified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, Hexane/EtOAc=95:5->0:100)

출처 및 근거

ORD 기록
ord-ace1d23199a04b408e2ae628f50aea31
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822468B2

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