Sodium hydride → Diethyl-4-(3-azidopropoxy)-2,6-pyridinedicarboxylate

HRID 392020ノート

反応式

HRID 392020 の反応式
[N:1]([CH2:4][CH2:5][CH2:6][OH:7])=[N+:2]=[N-:3].[H-].[Na+].[CH2:10]([O:12][C:13]([C:15]1[CH:20]=[C:19](Br)[CH:18]=[C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:16]=1)=[O:14])[CH3:11]>CN(C=O)C>[CH2:10]([O:12][C:13]([C:15]1[CH:20]=[C:19]([O:7][CH2:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])[CH:18]=[C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:16]=1)=[O:14])[CH3:11]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 109969743-Azidopropan-1-olHCID 13794409Diethyl 4-bromopyridine-2,6-dicarboxylate

生成物 1

HCID 22323654Diethyl-4-(3-azidopropoxy)-2,6-pyridinedicarboxylate収率 40%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

3-Azido-1-propanol (0.266 mL, 3.64 mmol) was dissolved in DMF (5 mL) and cooled to 0° C. NaH (146 mg, 3.64 mmol) was added and the mixture was stirred for 15 minutes. Diethyl-4-bromo-2,6-pyridinedicarboxylate dissolved in DMF (5 mL) was added to the reaction mixture dropwise. The reaction was complete as indicated by TLC in 1 hour. The reaction mixture was partitioned between CH2Cl2 and water. The water was separated and extracted with CH2Cl2. The CH2Cl2 layers were combined, dried (MgSO4) and concentrated to an oil. The oil was purified by silica gel flash column chromatography to give a yield of 40% of the title compound.

後処理

  1. additionwas added to the reaction mixture dropwise
  2. waitas indicated by TLC in 1 hour
  3. customThe reaction mixture was partitioned between CH2Cl2 and water
  4. customThe water was separated
  5. extractionextracted with CH2Cl2
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to an oil
  8. customThe oil was purified by silica gel flash column chromatography

出典と根拠

ORDレコード
ord-4aaa52ed25f447a8b5acc259498403ac
出典データセット
uspto-grants-2004_10
特許番号
US06800444B1

反応ノート

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