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

HRID 2203416노트

반응식

HRID 2203416 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3c864f4a5f4644cdb14002a6f68976d9
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365578B2

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