Water → HCID 68281577、化合物

HRID 2278593ノート

反応式

HRID 2278593 の反応式
Cl.C([N+](CCCC)(CCCC)CCCC)CCC.C(N(CC)CC)C.Br[C:27]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=1[N:34]([CH2:38][C:39]([CH3:41])=[CH2:40])[C:35](=[O:37])[CH3:36].O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:33][C:32]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:27]=1[C:39]([CH3:41])([CH3:40])[CH2:38][N:34]2[C:35](=[O:37])[CH3:36]

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 18314301HCID 18314301、化合物HCID 68281537HCID 68281537、化合物

生成物 1

HCID 68281577HCID 68281577、化合物収率 47.9%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

59 mg of palladium acetate, 1.5 g of tetrabutylammonium hydrochloride and 1.8 ml of triethylamine are added to a solution of 1.5 g of N-(2-bromo-3-fluorophenyl)-N-(2-methylallyl)acetamide in 10 ml of N,N-dimethylformamide. The reaction mixture is heated at 100° C. under an argon atmosphere for 16 hours. After cooling, 50 ml of water are added and the mixture is extracted with ethyl acetate. The organic phase is then washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica column chromatography, elution being carried out with a mixture of heptane and ethyl acetate (50/50: v/v), so as to give 520 mg of 1-(4-fluoro-3,3-dimethyl-2,3-dihydroindol-1-yl)ethanone in the form of a yellow oil.

後処理

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe organic phase is then washed with water
  4. dry with materiala saturated sodium chloride solution, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica column chromatography, elution
  8. additionbeing carried out with a mixture of heptane and ethyl acetate (50/50: v/v)

出典と根拠

ORDレコード
ord-60568b451da64059a9f41334e396e03b
出典データセット
uspto-grants-2015_09
特許番号
US09133168B2

反応ノート

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