Sodium hydride → (E)-allyl-[4-[1-(4-bromo-phenyl)-isoquinolin-6-yloxy]-but-2-enyl]-methyl-amine

HRID 342218

反応式

HRID 342218 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:22]/[CH:23]=[CH:24]/[CH2:25]Br.[CH2:27]([NH:30][CH3:31])[CH:28]=[CH2:29]>CN(C=O)C>[CH2:27]([N:30]([CH2:22]/[CH:23]=[CH:24]/[CH2:25][O:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[C:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)=[N:9][CH:10]=[CH:11]2)[CH3:31])[CH:28]=[CH2:29]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 69391N-MethylallylamineHCID 641245trans-1,4-Dibromo-2-buteneHCID 1361286691-(4-Bromo-phenyl)-isoquinolin-6-ol

生成物 1

HCID 67598888(E)-allyl-[4-[1-(4-bromo-phenyl)-isoquinolin-6-yloxy]-but-2-enyl]-methyl-amine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

A suspension of 0.5 g of 1-(4-bromo-phenyl)-isoquinolin-6-ol in 15 ml of DMF is cooled to 0° C. and treated with 0.15 g of ~55% sodium hydride. The mixture is stirred for 40 min., with a solution resulting. A solution of 0.39 g of (E)-1,4-dibromo-2-butene in 5 ml of DMF is added dropwise at -20° C. After stirring at -15° to -20° C. for 3 hrs. 0.8 ml of N-allyl-methyl-amine is added, the mixture is stirred overnight and warmed to room temperature. Subsequently, the reaction mixture is concentrated and the residue is treated with sodium hydrogen carbonate solution and extracted with methylene chloride. The organic extracts are washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated. The residue is chromatographed with toluene/acetone/triethylamine (90:9:1 to 70:29:1). There is obtained 0.1 g of (E)-allyl-[4-[1-(4-bromo-phenyl)-isoquinolin-6-yloxy]-but-2-enyl]-methyl-amine which is converted into the fumarate, MS: m/e 423 (M+H+, 1 Br).

後処理

  1. customresulting
  2. stirringAfter stirring at -15° to -20° C. for 3 hrs
  3. stirringthe mixture is stirred overnight
  4. temperaturewarmed to room temperature
  5. concentrationSubsequently, the reaction mixture is concentrated
  6. additionthe residue is treated with sodium hydrogen carbonate solution
  7. extractionextracted with methylene chloride
  8. washThe organic extracts are washed with saturated sodium chloride solution
  9. dry with materialdried over sodium sulphate
  10. concentrationconcentrated
  11. customThe residue is chromatographed with toluene/acetone/triethylamine (90:9:1 to 70:29:1)

出典と根拠

ORDレコード
ord-18e2085df2d24afb8f6098528773eb7e
出典データセット
uspto-grants-1999_01
特許番号
US05856503

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