Barium hydroxide, octahydrate → HCID 22024687、化合物

HRID 1793093ノート

反応式

HRID 1793093 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 22024687HCID 22024687、化合物収率 77.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8d298d32255543de800e4507a8f82d71
出典データセット
uspto-grants-2006_07
特許番号
US07078405B2

反応ノート

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