Triethylamine → 2-bromo-N-pyridin-2-yl-acetamide

HRID 2192335Notes

Reaction equation

HRID 2192335 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.CCN(CC)CC.[Br:15][CH2:16][C:17](Br)=[O:18]>C1COCC1>[Br:15][CH2:16][C:17]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 61147Bromoacetyl bromide

Product 1

HCID 34158372-bromo-N-pyridin-2-yl-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aminopyridine (48.8 mmol) in anhydrous THF (98 mL) at room temperature was added Et3N (58.6 mmol) and bromoacetyl bromide (58.6 mmol) dropwise The mixture was stirred overnight and quenched with sat. NaHCO3 (aq). EtOAc was added to the mixture and the layers separated. The aqueous phase was extracted with EtOAc and the combined organics dried (MgSO4) and concentrated in vacuo to a brown solid.

Workup

  1. customquenched with sat. NaHCO3 (aq)
  2. additionEtOAc was added to the mixture
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with EtOAc
  5. dry with materialthe combined organics dried (MgSO4)
  6. concentrationconcentrated in vacuo to a brown solid

Sources & evidence

ORD record
ord-6549214e493a46aa947896b6d4871768
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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