Pyridine → 9-(3-bromo-4-methylphenyl)-5,9-dihydro-3H-furo [3,4-b]pyrano[4,3-e]pyridine-1,8(4H,7H)-dione

HRID 478297노트

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HRID 478297 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13](C)[NH:12][C:11]3[CH2:20][O:21][CH2:22][C:23](=[O:24])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[CH3:8].N1C=CC=CC=1.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:10]3[C:23](=[O:24])[CH2:22][O:21][CH2:20][C:11]=3[NH:12][C:13]3[CH2:18][O:17][C:15](=[O:16])[C:14]2=3)[CH:5]=[CH:6][C:7]=1[CH3:8]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 18000988methyl 4-(3-bromo-4-methylphenyl)-2-methyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylateHCID 21124087Pyridiniumtribromide

생성물 1

HCID 102928969-(3-bromo-4-methylphenyl)-5,9-dihydro-3H-furo [3,4-b]pyrano[4,3-e]pyridine-1,8(4H,7H)-dione수율 49.8%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
-10 °C

실험 절차

The product from Example 68A (0.63 g, 1.6 mmol) in chloroform (10 mL) under a nitrogen atmosphere was treated with pyridine (0.16 mL, 1.9 mmol) and pyridinium tribromide (0.57 g, 1.8 mmol) at −10° C. After stirring at −10° C. for 2 hours, the mixture was allowed to warm to ambient temperature and then was treated with 1M HC1 and extracted with chloroform. The chloroform layer was dried (MgSO4), filtered, concentrated, heated to 130° C. under nitrogen for 1 hour and cooled to ambient temperature. Purification of the residue by chromatography on silica gel eluting with 10% methanol in dichloromethane provided the title compound (0.30 g).

후처리

  1. temperatureto warm to ambient temperature
  2. additionwas treated with 1M HC1
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. temperatureheated to 130° C. under nitrogen for 1 hour
  8. temperaturecooled to ambient temperature
  9. customPurification of the residue by chromatography on silica gel eluting with 10% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-0924c943dc634510a1f1a6a358a30579
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642222B2

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