1-Ethenyl-3-methylbenzene → HCID 69945928、化合物

HRID 724930ノート

反応式

HRID 724930 の反応式
[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]

参加物

8

反応物 3

HCID 75291-Ethenyl-3-methylbenzeneHCID 516892Sodium BicarbonateHCID 10547779HCID 10547779、化合物

生成物 1

HCID 69945928HCID 69945928、化合物収率 87.7%

試薬・触媒・溶媒 4

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0f3af44016464a439aa6424a5b78f39e
出典データセット
uspto-grants-1998_01
特許番号
US05705499

反応ノート

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