Tetrahydrofuran → 1-(6-Phenylimidazo[1,2-b]pyridazin-3-yl)-1-(quinolin-6-yl)ethanol

HRID 1513783Notes

Reaction equation

HRID 1513783 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:16]([C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[N:24]=[CH:23][CH:22]=[CH:21]5)=[O:17])=[CH:14][N:15]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:28]1COCC1.C[Mg]Br>Cl.O>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:16]([C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[N:24]=[CH:23][CH:22]=[CH:21]5)([OH:17])[CH3:28])=[CH:14][N:15]=3)[N:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 67502844(6-Phenylimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 576910551-(6-Phenylimidazo[1,2-b]pyridazin-3-yl)-1-(quinolin-6-yl)ethanolYield 39.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A 25 mL RB flask was charged with (6-phenylimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone (0.200 g, 0.57 mmol) and THF (2.00 ml, 24 mmol), then cooled to 0° C. methylmagnesium bromide (0.76 ml, 2.2 mmol) was added dropwise and the mixture was stirred at room temperature for 5 hours. This was diluted with 2 N HCl (1 mL) and water (25 mL), then extracted with DCM (25 mL×2) and EtOAc (25 mL). The combined organics were washed with brine and dried with MgSO4, filtered, and concentrated. The resulting oil was purified by MPLC using a 40 g RediSep column, eluting with 2-6% MeOH/DCM over 40 minutes. 1-(6-phenylimidazo[1,2-b]pyridazin-3-yl)-1-(quinolin-6-yl)ethanol (0.082 g, 39% yield) was isolated as a tan solid. MS (ESI pos. ion) m/z: 367 (MH+). Calc'd exact mass for C23H18N4O: 366.

Workup

  1. additionwas added dropwise
  2. extractionextracted with DCM (25 mL×2) and EtOAc (25 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting oil was purified by MPLC
  8. washeluting with 2-6% MeOH/DCM over 40 minutes

Sources & evidence

ORD record
ord-7729c3ff3da3423fa9d3ae6a63028ac3
Source dataset
uspto-grants-2012_07
Patent number
US08217177B2

Reaction notes

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