Sodium Methoxide → HCID 66937157, compound

HRID 1623297Notes

Reaction equation

HRID 1623297 reaction equation
[F:1][C:2]1[C:3]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[N:4][C:5](F)=[CH:6][CH:7]=1.[CH3:18][O-:19].[Na+]>CO.[Cl-].[Na+].O>[F:1][C:2]1[C:3]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[N:4][C:5]([O:19][CH3:18])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 66936980HCID 66936980, compound

Product 1

HCID 66937157HCID 66937157, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
150 °C

Procedure

3,6-difluoro-N-(3-fluorobenzyl)pyridine-2-amine (0.5209 g, 2.19 mmol), was dissolved in anhydrous MeOH (6.6 mL) and placed under argon. This mixture then was treated with sodium methoxide (0.500 mL, 0.473 g, 2.19 mmol, 25% in MeOH) by slow addition. The resulting mixture was then heated in the microwave at 150° C. for four 30 min. The reaction mixture was then poured into brine (25 mL). This mixture was extracted with EtOAc (3×25 mL), the combined extracts were washed with brine (1×25 mL) and dried (Na2SO4). After filtration the solvent removed in vacuo. The resulting residue was subjected to silica gel column chromatography. Elution using 100 hexanes to 25 EtOAc/75 hexanes afforded 0.3408 g (62%) of 3-fluoro-N-(3-fluorobenzyl)-6-methoxypyridin-2-amine. LCMS (m/z): 251.1 (MH+), retention time=1.07 min.

Workup

  1. extractionThis mixture was extracted with EtOAc (3×25 mL)
  2. washthe combined extracts were washed with brine (1×25 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationAfter filtration the solvent
  5. customremoved in vacuo
  6. washElution

Sources & evidence

ORD record
ord-bb61ec8e7c2d47a2974cc18489eadc6b
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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