Sodium hydride → 1-[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridin-3-yl]pyrrolidin-2-one

HRID 8799

반응식

HRID 8799 반응식
[H-].[Na+].Cl[CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[C:18]2[C:13](=[N:14][C:15]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=3[Cl:33])=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH:17]=2)[O:12][C:11]=1[C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[O:8]>C1COCC1>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[CH:17]=[C:18]3[C:10]([N:9]4[CH2:4][CH2:5][CH2:6][C:7]4=[O:8])=[C:11]([C:34](=[O:39])[C:35]([CH3:37])([CH3:36])[CH3:38])[O:12][C:13]3=[N:14][C:15]=2[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])=[CH:24][CH:23]=1

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 100996934-Chloro-N-[5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridin-3-yl]butanamide

생성물 1

HCID 100988381-[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridin-3-yl]pyrrolidin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
60 °C

실험 절차

To a magnetically stirred suspension of 7 mg (0.173 mmol) of sodium hydride in 1 mL THF was slowly added 0.100 g (0.173 mmol) of the product of Example 47 dissolved in 1 mL of THF. After 15 min the addition was complete and the reaction mixture was stirred and heated to 60° C. for 3.5 h. The reaction was then cooled to room temperature, and partitioned between saturated aq. NaHCO3 and EtOAc. The organic product was extracted into EtOAc, separated, dried (Na2SO4) filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0–20% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound. HPLC/MS: 541.0 (M+1), 542.9 (M+3); Rt=4.60 min.

후처리

  1. additionAfter 15 min the addition
  2. temperatureThe reaction was then cooled to room temperature
  3. custompartitioned between saturated aq. NaHCO3 and EtOAc
  4. extractionThe organic product was extracted into EtOAc
  5. customseparated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified on a silica gel flash chromatography column
  10. washeluted with 0–20% EtOAc-hexane
  11. customEvaporation of the purified fractions
  12. customdrying in vacuo

출처 및 근거

ORD 기록
ord-06ce1654413a4001b8df472ef7bcb703
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091216B2

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