Triethylamine → 2-bromo-N-pyridin-2-yl-acetamide
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
Product 1
Reagents, catalysts & solvents 1
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
- customquenched with sat. NaHCO3 (aq)
- additionEtOAc was added to the mixture
- customthe layers separated
- extractionThe aqueous phase was extracted with EtOAc
- dry with materialthe combined organics dried (MgSO4)
- 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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