Dimethylformamide → 6-Bromo-3-methoxyisoquinoline

HRID 880999Notes

Reaction equation

HRID 880999 reaction equation
[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

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 178515305HCID 178515305, compound

Product 1

HCID 674918076-Bromo-3-methoxyisoquinolineYield 14%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b99db38040a446c29ea69acec4fc38e6
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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