Tetrahydrofuran → 1-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)-1-(7-fluoroquinolin-6-yl)ethanol

HRID 1959659Notes

Reaction equation

HRID 1959659 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][C:22]=3[F:23])[N:19]=[CH:18][CH:17]=[CH:16]4)=[O:12])=[CH:9][N:10]=2)[N:7]=1.[CH2:24]1COCC1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][C:22]=3[F:23])[N:19]=[CH:18][CH:17]=[CH:16]4)([OH:12])[CH3:24])=[CH:9][N:10]=2)[N:7]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 58147533(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(7-fluoroquinolin-6-yl)methanone

Product 1

HCID 581475421-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)-1-(7-fluoroquinolin-6-yl)ethanolYield 95%

Procedure

To a solution of (6-chloroimidazo[1,2-b]pyridazin-3-yl)(7-fluoroquinolin-6-yl)methanone (2.93 g, 6.73 mmol) in THF (80 mL) was added MeMgl solution (3 M in THF, 4.48 mL, 13.45 mmol) and the resulting solution was stirred at reflux for 5 h. Then the reaction mixture was cooled to rt, quenched with water, washed with NH4Cl solution and extracted by DCM. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford 2.2 g (95%) of the title compound which was used to next step.

Workup

  1. temperatureat reflux for 5 h
  2. customquenched with water
  3. washwashed with NH4Cl solution
  4. extractionextracted by DCM
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4fe74bfff127469e88ea5d0f1ab2a170
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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