4-Vinylpyridine → HCID 86618523, compound

HRID 2239892Notes

Reaction equation

HRID 2239892 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:12]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]2[N:6]([C:8](I)=[CH:9][N:10]=2)[N:7]=1.[CH:28]([C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1)=[CH2:29]>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:3]=[C:4]([N:12]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]2[N:6]([C:8]([CH:29]=[CH:28][C:30]3[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=3)=[CH:9][N:10]=2)[N:7]=1

Participants

5

Reactant 2

HCID 75024-VinylpyridineHCID 866185226-chloro-3-iodo-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine

Product 1

HCID 86618523HCID 86618523, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

6-chloro-3-iodo-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine (120 mg, 0.25 mmol) from (1a), 4-vinylpyridine (54 μL, 0.50 mmol) and Pd(OAc)2 (23 mg, 0.1 mmole) in acetonitrile (1 mL) were heated at 85° C. for 2 h. After cooling to room temperature, the mixture was partitioned between EtOAc (200 mL) and water (20 mL) and the organic layer was washed with water, brine, then dried over MgSO4 and concentrated. The resulting residue was purified by flash chromatography to provide 6-chloro-N-(4-methoxybenzyl)-N-phenyl-3-(2-(pyridin-4-yl)vinyl)imidazo[1,2-b]pyridazin-8-amine as a yellow solid (75 mg, 66%). LCMS [M+H]+ 468.

Workup

  1. customthe mixture was partitioned between EtOAc (200 mL) and water (20 mL)
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-faf12db09c8c48fe9973a076211e0465
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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