Sodium Methoxide → HCID 58282711, compound

HRID 880811Notes

Reaction equation

HRID 880811 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[N:10]2)[N:3]=1.[CH3:18][O-:19].[Na+]>CO>[Cl:1][C:2]1[N:3]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[N:10]2)[N:5]=[C:6]([O:19][CH3:18])[CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58282694HCID 58282694, compound

Product 1

HCID 58282711HCID 58282711, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of compound 304 (1 g, 3.53 mmol) in MeOH (10 mL) at 0° C. was added NaOMe (760 μL) dropwise. The mixture was stirred at room temperature for 2 hrs. Methanol was evaporated. The residue was dissolved in DCM, washed sequentially with water and brine. Organics were dried over Na2SO4, filtered, concentrated under reduced pressure, and purified by silica gel chromatography to yield compound 305 as a white solid in 68% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 4.11 (s, 3H), 6.71-6.72 (m, 2H), 8.58 (dd, J=2.78 Hz and J=1.00 Hz, 1H); 19F NMR (CDCl3, 376 MHz) δ (ppm) −62.54 (s, 3F).

Workup

  1. customMethanol was evaporated
  2. dissolutionThe residue was dissolved in DCM
  3. washwashed sequentially with water and brine
  4. dry with materialOrganics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-c5dd79e7615b4b31a1ea88398b963c98
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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