Dimethylformamide → 6-Bromo-3-methoxyisoquinoline

HRID 880999ノート

反応式

HRID 880999 の反応式
[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

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 178515305HCID 178515305、化合物

生成物 1

HCID 674918076-Bromo-3-methoxyisoquinoline収率 14%

試薬・触媒・溶媒 2

HCID 178418647HCID 178418647、化合物触媒HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b99db38040a446c29ea69acec4fc38e6
出典データセット
uspto-grants-2015_03
特許番号
US08993586B2

反応ノート

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