Potassium Carbonate → 4-Cyano-4-[3-[4-(2-methylimidazol-1-yl)phenoxy]phenyl]-3,4,5,6-tetrahydro2H-pyran

HRID 1108110

반응식

HRID 1108110 반응식
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[C:14]([C:16]1([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)#[N:15].C([O-])([O-])=O.[K+].[K+]>N1C=CC=CC=1>[C:14]([C:16]1([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:10]3[CH:11]=[CH:12][C:7]([N:3]4[CH:4]=[CH:5][N:6]=[C:2]4[CH3:1])=[CH:8][CH:9]=3)[CH:23]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)#[N:15]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 112871604-Cyano-4-(3-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyranHCID 112890901-(4-iodophenyl)-2-methyl-1H-imidazole

생성물 1

HCID 113603734-Cyano-4-[3-[4-(2-methylimidazol-1-yl)phenoxy]phenyl]-3,4,5,6-tetrahydro2H-pyran수율 38.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
130 °C

실험 절차

A mixture of 4-(2-methylimidazol-1-yl)phenyl iodide (1.28 g, 4.5 mmol), 4-cyano-4-(3-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran (1.20 g, 5.9 mmol) and K2CO3 (4.15 g, 30 mmol) in pyridine (50 ml) was heated at 130° C., cupric oxide (636 mg, 8.0 mmol) added and the reaction mixture was heated under reflux for 2 days. The reaction mixture was cooled and filtered through a celite pad and the solids were washed with ethyl acetate (100 ml). The filtrate was concentrated in vacuo, and the resulting residue was diluted with water (100 ml) and extracted with ethyl acetate (50 ml×3). The combined organic extracts were washed with 1 N aqueous NaOH (100 ml), water (100 ml) and brine (100 ml), dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography {LiChroprep NH2 (Merck), 100 g; eluted with hexane/ethyl acetate (1/1)} to afford 620 mg (38%) of the titled compound as a yellow oil.

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 days
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through a celite pad
  5. washthe solids were washed with ethyl acetate (100 ml)
  6. concentrationThe filtrate was concentrated in vacuo
  7. additionthe resulting residue was diluted with water (100 ml)
  8. extractionextracted with ethyl acetate (50 ml×3)
  9. washThe combined organic extracts were washed with 1 N aqueous NaOH (100 ml), water (100 ml) and brine (100 ml)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by column chromatography {LiChroprep NH2 (Merck), 100 g
  13. washeluted with hexane/ethyl acetate (1/1)}

출처 및 근거

ORD 기록
ord-64f93b0d4fc14c01bd40747eb081d0c3
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06063928

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