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

HRID 456083Notes

Reaction equation

HRID 456083 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 8028TetrahydrofuranHCID 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 (4.48 mL, 13.45 mmol). The resulting solution was allowed to stir at reflux for 5 hrs. Then the reaction mixture was cooled to room temperature, quenched with water, washed with NH4Cl solution and extracted by CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford 2.2 g (yield: 95%) title compound which was used to next step without further purification. LCMS (method B): [MH]+=343, tR=2.05 min.

Workup

  1. temperatureat reflux for 5 hrs
  2. customquenched with water
  3. washwashed with NH4Cl solution
  4. extractionextracted by CH2Cl2
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3418903691884e0ead491a2ded421f91
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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