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Benzyl Bromide → 1-Benzyloxy-7-chloro-6-fluoro-isoquinoline

HRID 402521
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인쇄 미리보기

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HRID 402521 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][C:3]=1[F:13].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH2:14]([O:12][C:9]1[C:10]2[C:5](=[CH:4][C:3]([F:13])=[C:2]([Cl:1])[CH:11]=2)[CH:6]=[CH:7][N:8]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 7498Benzyl BromideHCID 598182487-Chloro-6-fluoroisoquinolin-1(2H)-one

생성물 1

HCID 598182521-Benzyloxy-7-chloro-6-fluoro-isoquinoline수율 54.2%

시약·촉매·용매 2

HCID 178418647HCID 178418647, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

14.74 g (74.6 mmol) of 7-chloro-6-fluoro-2H-isoquinolin-1-one (7) were dissolved in 150 ml of toluene. After addition of 30.86 g (111.9 mmol) of silver carbonate and 15.31 g (89.5 mmol) of benzyl bromide, the mixture was stirred at 80° C. for 3 h. After cooling down to room temperature, the reaction mixture was filtered and the filtrate was evaporated. The residue was dissolved in dichloromethane and washed with water, dried with magnesium sulfate and evaporated. Final purification by preparative HPLC gave 11.63 g of the title compound. Rt=2.51 min (Method B). Detected mass: 288.1/290.1 (M+H+).

후처리

  1. temperatureAfter cooling down to room temperature
  2. filtrationthe reaction mixture was filtered
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialdried with magnesium sulfate
  7. customevaporated
  8. customFinal purification by preparative HPLC

출처 및 근거

ORD 기록
ord-443867873dda4ba49a649b54c0bc50c0
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08742116B2

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