tert-Butoxy bis(dimethylamino)methane → 6-Fluoropyridine-2-carboxaldehyde

HRID 895531Notes

Reaction equation

HRID 895531 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.C([O:13]C(N(C)C)N(C)C)(C)(C)C.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[O:13])[N:3]=1

Participants

6

Reactant 3

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 960902-Fluoro-6-methylpyridineHCID 23667635Sodium periodate

Product 1

HCID 106067416-Fluoropyridine-2-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Fluoro-6-methylpyridine (14.4 g, 0.13 mol) and tert-butoxybis(dimethylamino)methane (Bredereck's reagent; 34.9 g, 0.20 mol) are heated at 140° C. for 24 h. The reaction is cooled and diluted with THF (100 mL). Sodium periodate (75 g) in water (400 mL) is added at 0-5° C., and the reaction mixture is then stirred for 24 h at room temperature. The precipitate is filtered through celite, and the filtrate extracted 5× with diethyl ether. The combined ether layers are washed with water, brine, and dried (MgSO4). Most of the solvent is removed by concentration at 0° C. (by keeping ice in the bath) to provide 2-Fluoropyridine-6-carboxaldehyde.

Workup

  1. temperatureThe reaction is cooled
  2. filtrationThe precipitate is filtered through celite
  3. extractionthe filtrate extracted 5× with diethyl ether
  4. washThe combined ether layers are washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customMost of the solvent is removed by concentration at 0° C. (

Sources & evidence

ORD record
ord-5deb7b4eedec4ea183b5f721b469c483
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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