tert-Butoxy bis(dimethylamino)methane → 2-Bromo-4-methylpyridine

HRID 1790323Notes

Reaction equation

HRID 1790323 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Br:8])[CH:3]=1.C(O[CH:14](N(C)C)[N:15]([CH3:17])[CH3:16])(C)(C)C>>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Br:8])[CH:3]=1.[Br:8][C:4]1[CH:3]=[C:2](/[CH:1]=[CH:14]/[N:15]([CH3:17])[CH3:16])[CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 27340872-Bromo-4-methylpyridine

Product 2

HCID 27340872-Bromo-4-methylpyridineHCID 22037380HCID 22037380, compound

Procedure

4-Methyl-2-bromopyridine (1.0 g, 5.8 mmol) and t-butoxybis(dimethylamino)methane (5 ml) were heated to 150° C. for 16 hours. 4-Methyl-2-bromopyridine was prepared as set forth in B. Adger et al., J. Chem. Soc., Perkin Trans. 1, pp. 2791-2796 (1988), which is incorporated herein by reference. The contents were evaporated and the residue dissolved in ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and solvent removed in vacuo to give 1.0 g of (E)-2-(2-bromo-4-pyridinyl)-N,N-dimethylethenamine as an oil suitable for use in step 2.

Workup

  1. customThe contents were evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate and solvent
  5. customremoved in vacuo

Sources & evidence

ORD record
ord-1c08ee51d78245dbbfb5572cd408d2d8
Source dataset
uspto-grants-2006_07
Patent number
US07071198B1

Reaction notes

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