2-Amino-5-bromopyridine → HCID 57413704, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:9][C:10]1[O:14][C:13]([CH2:15][CH2:16][C:17](Cl)=[O:18])=[CH:12][CH:11]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:17](=[O:18])[CH2:16][CH2:15][C:13]2[O:14][C:10]([CH3:9])=[CH:11][CH:12]=2)=[N:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5-bromopyridin-2-amine (123a, 600 mg, 3.47 mmol) in pyridine (10 ml) was added 3-(5-Methyl-furan-2-yl)-propionyl chloride (718.3 mg, 4.16 mmol) and stirred at room temperature for 16 hours. The reaction mixture was then quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give N-(5-Bromo-pyridin-2-yl)-3-(5-methyl-furan-2-yl)-propionamide (123): 1H NMR (500 MHz, DMSO) δ: 10.68 (s, 1H), 10.68 (s, 1H),8.42 (d, 1H), 8.07 (m, 1H), 5.94 (s, 1H), 5.92 (s, 1H), 2.85 (t, 2H), 2.70 (t, 2H), 2.19 (s, 3H). ESI-MS: 310.2 (M+H)+.