Stannane, tributyl(1-ethoxyethenyl)- → HCID 57917427, compound

HRID 69298Notes

Reaction equation

HRID 69298 reaction equation
Br[C:2]1[N:6]2[CH:7]=[C:8]([CH2:11][C:12]3[N:16]4[N:17]=[C:18]([C:21]5[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=5)[CH:19]=[CH:20][C:15]4=[N:14][CH:13]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:32]([O:34]CC)=[CH2:33])CCC>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:26][N:24]1[CH:25]=[C:21]([C:18]2[CH:19]=[CH:20][C:15]3[N:16]([C:12]([CH2:11][C:8]4[CH:9]=[CH:10][C:5]5[N:6]([C:2]([C:32](=[O:34])[CH3:33])=[CH:3][N:4]=5)[CH:7]=4)=[CH:13][N:14]=3)[N:17]=2)[CH:22]=[N:23]1

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 57917273HCID 57917273, compound

Product 1

HCID 57917427HCID 57917427, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

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, 100 mg, 0.245 mmol) was dissolved in dioxane (0.98 mL) in a microwave reactor. Then tributyl(1-ethoxyvinyl)tin (85 μL, 0.245 mmol) and tetrakis(triphenylphosphine)palladium (2.8 mg, 0.002 mmol) were introduced. The RM was heated at 150° C. for 1 h under microwave irradiations. The solvent was removed and the residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM). Combined fractions were concentrated and the residue was triturated with Et2O. The precipitate was filtered off and dried to afford the title compound as a white solid (tR 0.7 min (conditions 2), MH+=372).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM)
  3. concentrationCombined fractions were concentrated
  4. customthe residue was triturated with Et2O
  5. filtrationThe precipitate was filtered off
  6. customdried

Sources & evidence

ORD record
ord-25a69d2814e9479f972f70e53c0bb8ff
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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