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

HRID 42221ノート

反応式

HRID 42221 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-tetrahydrophthalazineHCID 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 (0.50 g, 2.46 mmol) in THF (5 mL) are added 4-fluoro-benzyl zinc chloride (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/Hexane: 10%˜40%) to give 1-chloro-4-(4-fluoro-benzyl)-5,6,7,8-tetrahydro-phthalazine (compound 10f) (0.51 g, 30%). m/z=277.11 [M+1]

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/Hexane: 10%˜40%)

出典と根拠

ORDレコード
ord-ae28a47084594912a3169b07dc9d979b
出典データセット
uspto-grants-2013_09
特許番号
US08536168B2

反応ノート

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