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

HRID 1942059Notes

Reaction equation

HRID 1942059 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.[CH3:24][Mg]Br.C(Cl)Cl.C([O-])(O)=O.[Na+]>C1COCC1.CCOCC>[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

7

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 58147533(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(7-fluoroquinolin-6-yl)methanoneHCID 178418573HCID 178418573, compound2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(7-fluoro-quinolin-6-yl)-methanone ((xiv), 294 mg, 0.9 mmol) was dissolved in anhydrous THF (70 mL) at 40° C. and methylmagnesium bromide in Et2O (3 M, 0.36 mL) was slowly added and the RM was then allowed to cool down to RT and stirred for 2 h. More methylmagnesium bromide in Et2O (3 M, 0.5 mL) was added and the RM was stirred for 1 h more. It was then taken into DCM and 10% aqueous NaHCO3 solution and extracted. The organic phase was dried on MgSO4. After evaporation of the solvent the crude was purified by flash chromatography to afford the title compound (tR 3.74 min (conditions 5), MH+=343, 1H-NMR in DMSO-d6: 8.87 (dd, 1H); 8.50 (d, 1H); 8.49 (d, 1H); 8.18 (d, 1H); 7.85 (s, 1H); 7.59 (d, 1H); 7.51 (dd, 1H); 7.23 (d, 1H); 6.33 (s, 1H); 2.13 (s, 3H)).

Workup

  1. stirringthe RM was stirred for 1 h more
  2. extractionextracted
  3. customThe organic phase was dried on MgSO4
  4. customAfter evaporation of the solvent the crude
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-ec71a34caaa14d0cb42374631c57eff9
Source dataset
uspto-grants-2013_03
Patent number
US08389526B2

Reaction notes

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