Sodium Methoxide → HCID 178488707, compound

HRID 40688Notes

Reaction equation

HRID 40688 reaction equation
F[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][C:8]([OH:12])=[CH:7]2.[CH3:13][O-:14].[Na+]>CN(C=O)C.CO>[CH3:13][O:14][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][C:8]([OH:12])=[CH:7]2

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 178515339HCID 178515339, compound

Product 1

HCID 178488707HCID 178488707, compoundYield 23.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

8-Fluoroisoquinolin-3-ol (561 mg, 3.43 mmol) was dissolved in DMF (3 mL) and sodium methoxide (828 mg, 15.33 mmol) added. The reaction mixture was heated at 90° C. for 14 hours, then diluted with methanol and absorbed onto an SPE (TsOH) cartridge. The column was rinsed with methanol and the compound was then eluted with 7 M ammonia in methanol to afford the title compound (140 mg, 0.798 mmol, 23.2%). LC-MS (2) Rt=1.23 min; m/z (ESI+) 176 (M+H).

Workup

  1. customabsorbed onto an SPE (TsOH) cartridge
  2. washThe column was rinsed with methanol
  3. washthe compound was then eluted with 7 M ammonia in methanol

Sources & evidence

ORD record
ord-64961ed9c98d4be496edbb2d18dcb634
Source dataset
uspto-grants-2013_09
Patent number
US08530468B2

Reaction notes

Loading…