1,4-Dichloro-5,6,7,8-tetrahydrophthalazine → 1-Chloro-4-(4-fluorobenzyl)-5,6,7,8-tetrahydrophthalazine

HRID 447108ノート

反応式

HRID 447108 の反応式
Cl[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([Cl:12])=[N:4][N:3]=1.[Cl-].[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][Zn+])=[CH:17][CH:16]=1>C1COCC1>[Cl:12][C:5]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[C:2]([CH2:19][C:18]2[CH:21]=[CH:22][C:15]([F:14])=[CH:16][CH:17]=2)=[N:3][N:4]=1

参加物

4

反応物 2

HCID 126224401,4-Dichloro-5,6,7,8-tetrahydrophthalazine2 回HCID 178505764HCID 178505764、化合物

生成物 1

HCID 574716251-Chloro-4-(4-fluorobenzyl)-5,6,7,8-tetrahydrophthalazine収率 74.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a solution of 1,4-dichloro-5,6,7,8-tetrahydro-phthalazine (compound 41, 0.50 g, 2.46 mmol) in THF (5 mL) are added 4-fluoro-benzyl zincchloride (0.5M in THF) (6.40 mL, 3.20 mmol) and palladium tetrakis triphenylphosphine (0.36 g, 0.31 mmol). The mixture is degassed and stirred at 50° C. overnight. Then the reaction mixture is cooled down to room temperature, sat. NaHCO3 and water are added and the mixture is extracted with EtOAc. The combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated down. The crude product is purified by chromatography (EtOAc/heptane: 10%˜40%) to give 1-chloro-4-(4-fluoro-benzyl)-5,6,7,8-tetrahydro-phthalazine (46) (0.51 g, 30%).

後処理

  1. customThe mixture is degassed
  2. temperatureThen the reaction mixture is cooled down to room temperature
  3. additionsat. NaHCO3 and water are added
  4. extractionthe mixture is extracted with EtOAc
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated down
  9. customThe crude product is purified by chromatography (EtOAc/heptane: 10%˜40%)

出典と根拠

ORDレコード
ord-7fcfd57bc694488fb59dffc481a67d04
出典データセット
uspto-grants-2013_07
特許番号
US08481542B2

反応ノート

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