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

HRID 42221노트

반응식

HRID 42221 반응식
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

참가 물질

4

반응물 2

HCID 126224401,4-Dichloro-5,6,7,8-tetrahydrophthalazineHCID 178505764HCID 178505764, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

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]

후처리

  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%)

출처 및 근거

ORD 기록
ord-ae28a47084594912a3169b07dc9d979b
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536168B2

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