Sodium hydride → 5-(2,4-Dimethylphenyl)-3-methyl-1-(1-propylbutyl)cinnolin-4(1H)-one

HRID 598161

반응식

HRID 598161 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11](=[O:20])[C:12]([CH3:19])=[N:13][NH:14]2.Br[CH:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25].[H-].[Na+]>CN1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11](=[O:20])[C:12]([CH3:19])=[N:13][N:14]2[CH:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 704604-BromoheptaneHCID 672672585-(2,4-Dimethylphenyl)-3-methylcinnolin-4(1H)-one

생성물 1

HCID 589385695-(2,4-Dimethylphenyl)-3-methyl-1-(1-propylbutyl)cinnolin-4(1H)-one수율 75%

시약·촉매·용매 1

HCID 84541-Methylpyrrolidine용매

실험 절차

To 0.041 g (0.16 mmol) of 5-(2,4-dimethylphenyl)-3-methylcinnolin-4(1H)-one in 0.5 mL of N-methylpyrrolidine was added 0.069 mL of 4-bromoheptane and 0.012 g (0.31 mmol) of sodium hydride (60% dispersion in mineral oil). The mixture was stirred for 75 min. at room temperature and quenched with water. The mixture was extracted with ethyl acetate and the combined organics were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography eluting with a 8% ethyl acetate/hexanes mixture to give 0.042 g (75%) of the title compound as a light green-yellow semisolid.

후처리

  1. customquenched with water
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined organics were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with a 8% ethyl acetate/hexanes mixture

출처 및 근거

ORD 기록
ord-4c6d66c81a604cbdb3c98764ce69fe95
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897607B2

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