Di-tert-butyl azodicarboxylate → HCID 67212506、化合物

HRID 1671347ノート

反応式

HRID 1671347 の反応式
Br[C:2]1[C:3]([CH3:19])=[N:4][N:5]2[C:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])=[C:8]([CH3:18])[O:7][C:6]=12.C([Li])CCC.[N:25]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[N:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>C1COCC1>[C:37]([O:36][C:34]([NH:25][N:26]([C:2]1[C:3]([CH3:19])=[N:4][N:5]2[C:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])=[C:8]([CH3:18])[O:7][C:6]=12)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:35])([CH3:40])([CH3:39])[CH3:38]

参加物

5

反応物 3

HCID 97268Di-tert-butyl azodicarboxylateHCID 67212702HCID 67212702、化合物HCID 178418339Butyllithium

生成物 1

HCID 67212506HCID 67212506、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a stirring solution of 7-bromo-3-(2,4-dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazole (710 mg, 1.972 mmol) in THF (15.5 ml) under N2 at −78° C. is added n-butyllithium (0.789 ml, 1.972 mmol) dropwise; the temperature is maintained below −70° C. for the addition and then the reaction mixture is stirred for 5 mins at −78° C. before the addition of di-tert-butyl azodicarboxylate (545 mg, 2.366 mmol) in THF (1.5 ml); the temperature is maintained below −60° C. for the period of the addition. After stirring at −78° C. for 30 mins, the reaction is quenched with sat. ammonium chloride solution and allowed to warm to RT. Ammonium chloride solution (sat.) is added and the mixture is extracted with EtOAc (2×100 ml). The combined organics extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified ISCO chromatography eluting (0 to 100%) EtOAci iso-hexane on a 40 g SiO2 cartridge to give the title compound as an orange solid; MS: m/z 511.22 [M+H]+

後処理

  1. temperaturethe temperature is maintained below −70° C. for the addition
  2. temperaturethe temperature is maintained below −60° C. for the period of the addition
  3. customthe reaction is quenched with sat. ammonium chloride solution
  4. temperatureto warm to RT
  5. additionAmmonium chloride solution (sat.) is added
  6. extractionthe mixture is extracted with EtOAc (2×100 ml)
  7. washThe combined organics extracts are washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe crude product is purified ISCO chromatography
  11. washeluting (0 to 100%) EtOAci iso-hexane on a 40 g SiO2 cartridge

出典と根拠

ORDレコード
ord-4f62b8207caa43c69c4b48c76a52ad8b
出典データセット
uspto-grants-2011_08
特許番号
US07994203B2

反応ノート

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