Potassium Carbonate → (4-Chloro-2-fluorophenyl)(6-chloro-2-methyl-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-3-yl)methanone

HRID 597859Notes

Reaction equation

HRID 597859 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]2[N:5]([C:10]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[F:23])=[O:15])=[C:11]([CH3:13])[N:12]=2)[N:6]=[C:7]([Cl:9])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH2:32][O:33][CH2:34][CH2:35]Br>O>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]([C:10]2[N:5]3[N:6]=[C:7]([Cl:9])[CH:8]=[C:3]([CH2:2][N:1]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[C:4]3=[N:12][C:11]=2[CH3:13])=[O:15])=[C:17]([F:23])[CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 86642486(8-(Aminomethyl)-6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)(4-chloro-2-fluorophenyl)methanone

Product 1

HCID 56954584(4-Chloro-2-fluorophenyl)(6-chloro-2-methyl-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-3-yl)methanoneYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Combine (8-(aminomethyl)-6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)(4-chloro-2-fluorophenyl)methanone (1.15 g, 3.3 mmol), water (12 mL), potassium carbonate (495 mg, 1.1 equiv.), and 2-bromoethyl ether (0.47 mL, 1.1 equiv) in a 20 mL microwave reaction vessel. Seal with a crimp cap then heat in a microwave reactor at 120° C. for 20 min. Cool to RT and partition between EA and water. Wash EA layer with aqueous saturated sodium chloride, and dry over anhydrous magnesium sulfate. Filter and concentrate in vacuo. Purify on silica gel (4:1 hexane:EA→2:1 hexane:EA→1:1 hexane:EA) to give the title compound (0.43 g, 31%) as a light yellow foam. LCMS (4 min)=423.0, 425.0, M+1.

Workup

  1. customSeal with a crimp
  2. customcap
  3. temperatureCool to RT
  4. custompartition between EA and water
  5. dry with materialWash EA layer with aqueous saturated sodium chloride, and dry over anhydrous magnesium sulfate
  6. filtrationFilter
  7. concentrationconcentrate in vacuo
  8. customPurify on silica gel (4:1 hexane

Sources & evidence

ORD record
ord-c2bd167adc814fdfa0ba855d89d559f3
Source dataset
uspto-grants-2011_03
Patent number
US07897600B2

Reaction notes

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