Potassium methoxide → HCID 89837067, compound

HRID 1054891Notes

Reaction equation

HRID 1054891 reaction equation
[CH3:1][O-:2].[K+].[Br:4][C:5]1[CH:6]=[CH:7][C:8]([N:12]([CH3:14])[CH3:13])=[N:9][C:10]=1F>[Cl-].[NH4+]>[Br:4][C:5]1[CH:6]=[CH:7][C:8]([N:12]([CH3:14])[CH3:13])=[N:9][C:10]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 23664618Potassium methoxideHCID 90421671HCID 90421671, compound

Product 1

HCID 89837067HCID 89837067, compound

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of potassium methoxide (25% in methanol, 74.2 mL, 251 mmol) was added Intermediate (5-bromo-6-fluoro-pyridin-2-yl)-dimethyl-amine (18.36 g, 83.8 mmol). The reaction was stirred at reflux for 3 h before cooling to room temperature. The contents were poured into a solution of saturated ammonium chloride (500 mL) and this was extracted with ethyl acetate (3×300 mL). The combined organics were washed with brine (250 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford desired product as an oil that solidified upon standing to give an off white/yellow solid (18.3 g, 95% yield). 1H NMR (CDCl3, 400 MHz) 5=7.49 (d, J=8.59 Hz, 1 H) 5.95 (d, J=8.59 Hz, 1 H) 3.96 (s, 3 H) 3.05 (s, 6 H); MS (FID)=230.1 (M)+.

Workup

  1. temperatureat reflux for 3 h
  2. extractionthis was extracted with ethyl acetate (3×300 mL)
  3. washThe combined organics were washed with brine (250 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b9f0665de74430a81cb37f0ed45a670
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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