Triethylamine → N-(6-bromo-2-pyridinyl)-3-methylbut-2-enamide

HRID 887597

Reaction equation

HRID 887597 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.CCN(CC)CC.[CH3:16][C:17]([CH3:22])=[CH:18][C:19](Cl)=[O:20]>C(Cl)Cl>[Br:8][C:4]1[N:3]=[C:2]([NH:1][C:19](=[O:20])[CH:18]=[C:17]([CH3:22])[CH3:16])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1023943-Methyl-2-butenoyl chlorideHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 43520526N-(6-bromo-2-pyridinyl)-3-methylbut-2-enamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-6-bromopyridine (3.015 g, 0.017 mol) and Et3N (2.40 mL, 0.017 mol) in CH2Cl2 (20.0 mL), was added 3,3-dimethylacryloylchloride (1.96 mL, 0.017 mol) under N2 at 0° C. The mixture was slowly warmed to RT and stirred for 12 h. The reaction was quenched by the addition of H2O (20.0 mL), the organic layer was separated, dried over Na2SO4 and evaporated to dryness to yield crude compound which was used without purification.

Workup

  1. customThe reaction was quenched by the addition of H2O (20.0 mL)
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customto yield crude compound which
  6. customwas used without purification

Sources & evidence

ORD record
ord-075960414edf481099c04b6dcf2897ff
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Linked notes

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