Reaction #156478

Reaction equation

3-(3-Bromo-imidazo[1,2-a]pyridin-6-ylmethyl)-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

tributyl(vinyl)tin

→

title compound

6-(1-Methyl-1H-pyrazol-4-yl)-3-(3-vinyl-imidazo[1,2-a]pyridin-6-ylmethyl)-imidazo[1,2-b]pyridazine

Solvents

dioxane

Conditions

Workup

1. 1
   OtherThe solvent was removed
2. 2
   OtherThe residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA)
3. 3
   workup.DISSOLUTIONThe residue was dissolved in MeOH
4. 4
   Otherto remove the TFA salt
5. 5
   OtherThe filtrate was evaporated

Procedure

3-(3-Bromo-imidazo[1,2-a]pyridin-6-ylmethyl)-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine (Example 296, 50 mg, 0.122 mmol) was dissolved in dioxane (0.5 mL) in a microwave reactor. Then tributyl(vinyl)tin (36.9 μL, 0.122 mmol) and tetrakis(triphenylphosphine)palladium (1.4 mg, 0.001 mmol) were introduced. The RM was heated at 150° C. for 30 min under microwave irradiations. The solvent was removed and The residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA). The fractions were joined and were lyophilized. The residue was dissolved in MeOH and it was passed through an SPE cartridge of HCO3− to remove the TFA salt. The filtrate was evaporated to give the free salt of the title compound as a yellow solid (tR 0.7 min (conditions 2), MH+=356).

Source