1-Ethenyl-3-methylbenzene → HCID 69945928, 화합물

HRID 724930노트

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HRID 724930 반응식
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12](I)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2].[CH3:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=[CH2:26].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([CH:26]=[CH:25][C:24]3[CH:23]=[C:22]([CH3:21])[CH:29]=[CH:28][CH:27]=3)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2]

참가 물질

8

반응물 3

HCID 75291-Ethenyl-3-methylbenzeneHCID 516892Sodium BicarbonateHCID 10547779HCID 10547779, 화합물

생성물 1

HCID 69945928HCID 69945928, 화합물수율 87.7%

시약·촉매·용매 4

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

A mixture of 5,11-dihydro-11-ethyl-8-iodo-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.15 g, 0.4 mmol), 3-methylstyrene (0.05 mL, 0.4 mmol), palladium acetate (29 mg, 0.13 mmol), sodium bicarbonate (83 mg, 1.0 mmol), tetrabutylammonium chloride (0.11 g, 0.47 mmol), and 1 crystal of BHT in 2 mL of N,N-dimethylformamide was heated at 90° C. under argon for 4.5 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (magnesium sulfate), and concentrated. Purification by flash chromatography, eluting with ethyl acetate/hexanes, afforded 0.13 g of the title compound, m.p. 207°-208° C. (ethyl acetate/hexanes).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customPurification by flash chromatography
  6. washeluting with ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-0f3af44016464a439aa6424a5b78f39e
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05705499

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