Sodium Carbonate → 5-(5-Chloro-2-methoxyphenyl)imidazo[1,2-a]pyridine

HRID 2203416ノート

反応式

HRID 2203416 の反応式
[ClH:1].Cl[C:3]1[N:8]2[CH:9]=[CH:10][N:11]=[C:7]2[CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].O1[CH2:23][CH2:22][O:21][CH2:20]C1>C(OCC)(=O)C.O.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>[Cl:1][C:4]1[CH:5]=[CH:6][C:22]([O:21][CH3:20])=[C:23]([C:3]2[N:8]3[CH:9]=[CH:10][N:11]=[C:7]3[CH:6]=[CH:5][CH:4]=2)[CH:3]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 219941745-Chloroimidazo[1,2-a]pyridine hydrochloride

生成物 1

HCID 895442625-(5-Chloro-2-methoxyphenyl)imidazo[1,2-a]pyridine収率 70%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred mixture of 5-chloroimidazo[1,2-a]pyridine hydrochloride (1.89 g, 10.0 mmol), (5-chloro-2-methoxy)benzene boronic acid (2.07 g, 12.0 mmol), 2 M aqueous sodium carbonate (20 mL, 40 mmol) and p-dioxane (50 mL) was added tetrakis(triphenylphosphine)palladium(0) (0.58 g, 0.50 mmol) at ambient temperature. The mixture was heated at reflux for 16 h, allowed to cool to ambient temperature and diluted with ethyl acetate (50 mL) and water (20 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 50-80% gradient of ethyl acetate in hexanes to afford 5-(5-chloro-2-methoxyphenyl)imidazo[1,2-a]pyridine as a colorless solid in 70% yield (1.82 g): 1H NMR (300 MHz, DMSO-d6) δ7.72-7.48 (m, 4H), 7.37-7.23 (m, 3H), 6.89 (d, J=6.6 Hz, 1H), 3.74 (s, 3H); MS (ES+) m/z 259.0 (M+1), 261.0 (M+1).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluting with a 50-80% gradient of ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-3c864f4a5f4644cdb14002a6f68976d9
出典データセット
uspto-grants-2016_06
特許番号
US09365578B2

反応ノート

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