Barium hydroxide, octahydrate → HCID 22024687, compound

HRID 1793093Notes

Reaction equation

HRID 1793093 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:8]([C:13](=[O:17])[CH2:14][CH2:15][CH3:16])=[C:9]([CH2:11][CH3:12])[N:10]=2)[CH:5]=[CH:6][N:7]=1.[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[C:22](B(O)O)=[C:21]([O:29][CH3:30])[CH:20]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>COCCOC.O>[CH2:11]([C:9]1[N:10]=[C:3]2[C:2]([C:20]3[C:19]([CH3:18])=[CH:24][C:23]([CH3:25])=[CH:22][C:21]=3[O:29][CH3:30])=[N:7][CH:6]=[CH:5][N:4]2[C:8]=1[C:13](=[O:17])[CH2:14][CH2:15][CH3:16])[CH3:12]

Participants

6

Reactant 3

HCID 17749109Barium hydroxide, octahydrateHCID 21931520(2-Methoxy-4,6-dimethylphenyl)boronic acidHCID 22024494HCID 22024494, compound

Product 1

HCID 22024687HCID 22024687, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

1-(8-Chloro-2-ethylimidazo[1,2-a]pyrazin-3-yl)-1-butanone (226 mg, 0.90 mmol) and 4,6-dimethyl-2-methoxybenzeneboronic acid (198 mg, 1.1 mmol) were dissolved in a mixed solvent of 1,2-dimethoxyethane (4.5 mL) and water (0.75 mL). Barium hydroxide octahydrate (347 mg, 1.1 mmol) and tetrakis(triphenylphosphine)palladium complex (79 mg, 0.068 mmol) were added thereto, and the mixture was heated under reflux for 4 hours under nitrogen atmosphere. After being allowed to cool, the reaction mixture was filtered and washed with ethyl acetate. Then, the filtrates were combined and washed with a 1N aqueous sodium hydroxide solution. It was extracted with ethyl acetate and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3) to give 1-[2-ethyl-8-(2-methoxy-4,6-dimethylphenyl)imidazo[1,2-a]pyrazin-3-yl]-1-butanone (245 mg) as a white amorphous.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours under nitrogen atmosphere
  3. temperatureto cool
  4. filtrationthe reaction mixture was filtered
  5. washwashed with ethyl acetate
  6. washwashed with a 1N aqueous sodium hydroxide solution
  7. extractionIt was extracted with ethyl acetate
  8. customevaporated
  9. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-8d298d32255543de800e4507a8f82d71
Source dataset
uspto-grants-2006_07
Patent number
US07078405B2

Reaction notes

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