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 478297ノート

反応式

HRID 478297 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
-10 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0924c943dc634510a1f1a6a358a30579
出典データセット
uspto-grants-2003_11
特許番号
US06642222B2

反応ノート

読み込み中…