1-Bromo-3-methylbutane → Ethyl 1-isopentyl-4-nitro-1H-pyrrole-2-carboxylate

HRID 644800

反応式

HRID 644800 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:7][CH:8]=1)([O-:3])=[O:2].[K].[CH2:15](Br)[CH2:16][CH:17]([CH3:19])[CH3:18]>CN(C=O)C>[CH2:15]([N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:16][CH:17]([CH3:19])[CH3:18]

参加物

5

反応物 3

HCID 78911-Bromo-3-methylbutaneHCID 242169Ethyl 4-Nitropyrrole-2-carboxylateHCID 5462222Potassium

生成物 1

HCID 67183320Ethyl 1-isopentyl-4-nitro-1H-pyrrole-2-carboxylate収率 85.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Ethyl 4-nitro-1H-pyrrole-2-carboxylate (2.022 g, 10.983 mmol; see Example 1, step (i) above) was dissolved in DMF (30 mL, dry) to which potassium (0.569 g, 14.552 mmol) was added with stirring under nitrogen. The reaction mixture was heated at 100° C. for 1 h and then the temperature was allowed to reach 50° C. Isoamyl bromide (2.498 g, 16.538 mmol) was then added, followed by KI (2.197 g, 14.552 mmol). The temperature was raised to 100° C. and stirring continued for 5 h, after which time the temperature was allowed to return to room temperature. The reaction mixture was then stirred overnight, following which the solvent was removed under reduced pressure at 50° C. The crude product was dissolved in DCM and the salt extracted with water. The organic extract was dried over MgSO4, filtered and the solvent removed under reduced pressure at 30° C. The crude product obtained was chromatographed over silica gel using 1/2 n-hexane/DCM as eluant. Material with Rf=0.3 was collected and the solvent was removed under reduced pressure to give white crystalline material (2.377 g, 85% yield). M.p. 46-47° C. (Lit. m.p. 46-47° C.).

後処理

  1. additionwas added
  2. customto reach 50° C
  3. temperatureThe temperature was raised to 100° C.
  4. stirringstirring
  5. customto return to room temperature
  6. stirringThe reaction mixture was then stirred overnight
  7. customwas removed under reduced pressure at 50° C
  8. dissolutionThe crude product was dissolved in DCM
  9. extractionthe salt extracted with water
  10. extractionThe organic extract
  11. dry with materialwas dried over MgSO4
  12. filtrationfiltered
  13. customthe solvent removed under reduced pressure at 30° C
  14. customThe crude product obtained
  15. customwas chromatographed over silica gel using 1/2 n-hexane/DCM as eluant
  16. customMaterial with Rf=0.3 was collected
  17. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-865a6b2724cd424aa18d4080505407b1
出典データセット
uspto-grants-2010_04
特許番号
US07700765B2

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