4-Chlorophenol → Methyl 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylate

HRID 1977408노트

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HRID 1977408 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9]C(C)([O-])C.[K+].Cl[C:16]1[CH:17]=[N:18][CH:19]=[C:20](Cl)[C:21]=1[CH:22]=O.C[CH:26]([SH:30])[C:27]([O-:29])=[O:28].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:20]2[CH:19]=[N:18][CH:17]=[C:16]3[S:30][C:26]([C:27]([O:29][CH3:9])=[O:28])=[CH:22][C:21]=23)=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 46844-ChlorophenolHCID 10796Cesium carbonateHCID 27629883,5-Dichloro-4-pyridinecarboxaldehydeHCID 156077362-MercaptopropionateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 10892544Methyl 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
25 °C

실험 절차

A solution of 4-chlorophenol (2.63 g, 20.5 mmol) in THF (20 mL) at 0° C. was treated dropwise with a solution of potassium tert-butoxide (1.0 M solution in THF, 20.4 mL, 20.5 mmol), stirred at 25° C. for 1 hour, cooled to 0° C., treated with a solution of Example 17A (3.54 g, 20.23 mmol) in THF (40 mL), warmed at 60° C. for 0.5 hours, cooled to 0° C., treated with methylthioglycolate (1.989 mL, 22.25 mmol) and Cs2CO3 (6.59 g, 20.23 mmol), warmed at 60° C. for 0.25 hours, cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate, washed sequentially with water and brine, dried (MgSO4), filtered, and concentrated. Purification of the residue by flash chromatography on silica gel with 4% acetone/hexane provided the title compound.

후처리

  1. temperaturecooled to 0° C.
  2. temperaturewarmed at 60° C. for 0.5 hours
  3. temperaturecooled to 0° C.
  4. temperaturewarmed at 60° C. for 0.25 hours
  5. temperaturecooled to room temperature
  6. filtrationfiltered
  7. additionThe filtrate was diluted with ethyl acetate
  8. washwashed sequentially with water and brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification of the residue by flash chromatography on silica gel with 4% acetone/hexane

출처 및 근거

ORD 기록
ord-4aa5b9a27a5f4f1db42c118260a2621f
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06232320B1

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