Potassium Carbonate → N-(4-fluorobenzyl)-5-(6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline

HRID 539734Notes

Reaction equation

HRID 539734 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2=[N:9][C:10]([C:12]3[CH:13]=[CH:14][C:15]([CH3:19])=[C:16]([CH:18]=3)[NH2:17])=[CH:11][N:5]2[N:4]=1.C([O-])([O-])=O.[K+].[K+].[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1>C(#N)C>[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH:17][C:16]2[CH:18]=[C:12]([C:10]3[N:9]=[C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[N:4][N:5]4[CH:11]=3)[CH:13]=[CH:14][C:15]=2[CH3:19])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 529038205-(6-Methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline

Product 1

HCID 57406703N-(4-fluorobenzyl)-5-(6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylanilineYield 34.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An 8 mL vial is charged with 5-(6-methoxyimidazo[2,1-f]pyridazin-2-yl)-2-methyl-aniline (20.3 mg, 0.08 mmol) in acetonitrile (0.5 mL), K2CO3 (13 mg) and 4-fluorobenzyl bromide (19 mg, 0.1 mmol). The mixture is stirred for 30 min then filtered, and the filtrate is added into water (10 mL). Solids precipitated and are collected by filtration to give the title compound (10 mg, 34% yield) (compound same as Example 102). LCMS m/z=363.3 [M+H]+, tR=2.57 min.

Workup

  1. filtrationthen filtered
  2. additionthe filtrate is added into water (10 mL)
  3. customSolids precipitated
  4. filtrationare collected by filtration

Sources & evidence

ORD record
ord-c7136958642448089aea0666db0ba728
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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