Sodium Methoxide → 2-Fluoro-4-iodo-6-methoxypyridine

HRID 1253562Notes

Reaction equation

HRID 1253562 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4](F)[N:3]=1.[CH3:10][O-:11].[Na+]>O1CCCC1.CO>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([O:11][CH3:10])[N:3]=1

Participants

5

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 217473652,6-Difluoro-4-iodopyridine

Product 1

HCID 672052392-Fluoro-4-iodo-6-methoxypyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-difluoro-4-iodopyridine (7.37 g, 30.6 mmol) in tetrahydrofuran (200 ml) cooled to 0° C. was added a 0.5 M solution of sodium methoxide (61.2 ml, 30.6 mm) in methyl alcohol. After 4 h the reaction mixture was warmed to ambient temperature. LRMS indicated incomplete conversion to product and additional 0.5 M sodium methoxide solution in methyl alcohol (6.12 ml, 3.06 mmol) was added. After 1 hour the reaction mixture was quenched with water (50 ml), partially concentrated, diluted with ethyl ether, washed with water and brine, then dried over magnesium sulfate, filtered, and concentrated to afford 2-fluoro-4-iodo-6-methoxypyridine as a yellow oil which was used without further purification. 1H NMR (600 MHz, DMSO-d6) δ 7.19 (s, 1H); 7.16 (d, 1H); 3.78 (s, 3H).

Workup

  1. additionwas added
  2. customAfter 1 hour the reaction mixture was quenched with water (50 ml)
  3. concentrationpartially concentrated
  4. additiondiluted with ethyl ether
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-62727eb34ab44df894d47c19e3aaa241
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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