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

HRID 861046Notes

Reaction equation

HRID 861046 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-7fa78fac6cc14fd9a32b463e9186862f
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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