戴斯-马丁氧化剂 → 6,11-Dihydro-5H-dipyrido[2,3-b:3',4'-f]azepin-5-one

HRID 75208

反应方程式

HRID 75208 反应方程式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[N:23]1[C:28]2[NH:29][C:30]3[CH:38]=[CH:37][N:36]=[CH:35][C:31]=3[CH2:32][CH:33]([OH:34])[C:27]=2[CH:26]=[CH:25][CH:24]=1.S(=O)(=O)(O)[O-].[Na+]>ClCCl.O.C(=O)(O)[O-].[Na+]>[N:23]1[C:28]2[NH:29][C:30]3[CH:38]=[CH:37][N:36]=[CH:35][C:31]=3[CH2:32][C:33](=[O:34])[C:27]=2[CH:26]=[CH:25][CH:24]=1

参与物

7

反应物 3

HCID 159087戴斯-马丁氧化剂HCID 516919硫酸氢钠HCID 668863896,11-Dihydro-5H-dipyrido[2,3-b:3',4'-f]azepin-5-ol

产物 1

HCID 668868736,11-Dihydro-5H-dipyrido[2,3-b:3',4'-f]azepin-5-one收率 90%

试剂、催化剂与溶剂 3

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6344二氯甲烷溶剂2 次HCID 516892碳酸氢钠溶剂

实验过程

Dess-Martin periodinane (0.810 g, 1.91 mmol) was added to a solution of 6,11-dihydro-5H-dipyrido[2,3-b:3′,4′-f]azepin-5-ol (0.370 g, 1.74 mmol, Intermediate D-5) in dichloromethane (30 mL) under an atmosphere of nitrogen and stirred for 1 h. The yellow mixture was poured into a solution of sodium bisulfate in water and stirred for 5 minutes. The mixture was then diluted with dichloromethane and sodium bicarbonate was added to adjust the pH to 8-9. The mixture was extracted three times with dichloromethane and the combined extracts were dried over sodium sulfate, filtered, and concentrated. The crude product residue was adsorbed onto silica gel and chromatographed on a silica gel column eluting with 10% methanol/dichloromethane to provide the desired product as a light tan solid (330 mg, 90%). 1H NMR (DMSO-d6): δ 10.55 (s, 1H), 8.51 (dd, 1H), 8.42 (s, 1H), 8.35 (d, 1H), 8.18 (dd, 1H), 7.33 (d, 1H), 7.06 (dd, 1H), 3.82 (s, 2H). LC/MS: 212 (M+H)+.

后处理

  1. stirringstirred for 5 minutes
  2. additionwas added
  3. extractionThe mixture was extracted three times with dichloromethane
  4. dry with materialthe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on a silica gel column
  8. washeluting with 10% methanol/dichloromethane

来源与证据

ORD记录
ord-4cc63b5c2c2540fda0eedca268d15367
来源数据集
uspto-grants-2014_09
专利号
US08835423B2

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