Water → N-(5-bromo-2-methylpyridin-3-yl)acetamide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([CH3:8])=[N:6][CH:7]=1.N1C=CC=CC=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:16](=[O:18])[CH3:17])[C:5]([CH3:8])=[N:6][CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 5-bromo-2-methylpyridin-3-amine (3.2 g, 17 mmol) in dichloromethane (100 mL) was added pyridine (2.03 g, 25.7 mmol) and acetic anhydride (2.63 g, 25.7 mmol). The mixture was stirred at 80° C. for 16 h. The mixture was poured into water (80 mL) and extracted with dichloromethane (3×150 mL). The organic layer was concentrated in vacuo, and the resultant residue was purified by flash column chromatography (15→30% ethyl acetate in petroleum ether) to afford N-(5-bromo-2-methylpyridin-3-yl)acetamide (3.1 g, 80% yield). 1H NMR (400 MHz, Chloroform-d) δ 8.48 (s, 1 H), 8.32 (s, 1 H), 7.09 (br s. 1 H), 2.45 (s, 3 H), 2.23 (s, 3 H).
Workup
- extractionextracted with dichloromethane (3×150 mL)
- concentrationThe organic layer was concentrated in vacuo
- customthe resultant residue was purified by flash column chromatography (15→30% ethyl acetate in petroleum ether)
Sources & evidence
- ORD record
- ord-657550eb073544f3a5e9186bca8163de
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365583B2
Reaction notes
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