Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[N:3]=1.O.[NH3:14]>>[NH2:14][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[N:3]=1Participants
Procedure
To a mixture of 2-bromo-6-(1H-pyrazol-1-yl)pyridine (3.0 mmol, 669 mg) and Cu2O (0.01 mmol, 1.0 mg) in glycol in autoclave NH3 was feed. The reaction was maintained under 10 atm of NH3 at 110° C. for 24 h. After cooling to room temperature, water was added and the aqueous phase was extracted with DCM. The combined organic layers were washed with brine and dried over MgSO4. After solvent evaporation, the crude product was purified by column chromatography on silica gel (Hexanes:ethyl acetate=6:1 as eluent) to afford a white solid (388 mg, 81% yield). 1H NMR (400 MHz, CDCl3, ppm): 8.44 (s, 1H), 7.69 (s, 1H), 7.53 (m, 1H), 7.28 (m, 1H), 6.42-6.37 (m, 2H), 4.49 (br, 2H). 13C NMR (100 MHz, CDCl3, ppm): 151.45, 142.72, 140.73, 139.91, 127.58, 125.25, 110.89, 108.23.
Workup
- extractionthe aqueous phase was extracted with DCM
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- customAfter solvent evaporation
- customthe crude product was purified by column chromatography on silica gel (Hexanes:ethyl acetate=6:1 as eluent)
Sources & evidence
- ORD record
- ord-4fa80ff0e1c7418bb04267cf989f3656
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598351B2
Linked notes
Loading…