Dimethylformamide → 6-Bromo-3-methoxyisoquinoline

HRID 880999노트

반응식

HRID 880999 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([OH:12])=[CH:5]2.[CH3:13]N(C)C=O.CI>CO.C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([O:12][CH3:13])=[CH:5]2

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 178515305HCID 178515305, 화합물

생성물 1

HCID 674918076-Bromo-3-methoxyisoquinoline수율 14%

시약·촉매·용매 2

HCID 178418647HCID 178418647, 화합물촉매HCID 887Methanol용매

실험 절차

A mixture of 6-bromoisoquinolin-3-ol (606 mg, 2.70 mmol), silver carbonate (1.5 g, 5.3 mmol), and N,N-dimethylformamide (12 mL) was stirred at room temperature for 16 minutes. Methyl iodide (186 μL, 2.97 mmol) was added and the reaction was left stirring for 18 hours. The reaction was diluted with methanol and filtered through Celite. The filtrate was concentrated and purified by flash column chromatography to give the title compound (90 mg, 14%). +ESI (M+H+1) 240.0; 1H NMR (400 MHz, CDCl3, δ): 8.91 (s, 1H), 7.86 (d, J=1.8 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.43 (dd, J=8.8, 1.8 Hz, 1H), 6.90 (s, 1H), 4.02 (s, 3H).

후처리

  1. waitthe reaction was left
  2. stirringstirring for 18 hours
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated
  5. custompurified by flash column chromatography

출처 및 근거

ORD 기록
ord-b99db38040a446c29ea69acec4fc38e6
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993586B2

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