Hexahydro-1,4-diazepine → 1-(5-Bromopyridin-2-yl)-1,4-diazepane
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.[NH:9]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5-Bromo-2-fluoro-pyridine (2.0 g, 11.4 mmol), [1,4]Diazepane (2.2 g, 22.8 mmol) in CH3CN (5.0 mL) was stirred at 50° C. for 3 hrs. Filter of the solid and the mother solution was brine, and concentrated in vacuo to give the title product (1.47 g, 51%) as a brown solid. ESI MS m/z 256 (M+H+); 1H NMR (400 MHz, CDCl3) δ 8.12 (d, J=7.0 Hz, 1H), 7.45 (dd, J=22.0, 6 Hz, 1H), 6.38 (d, J=22.0 Hz, 1H), 3.66 (m, 4H), 2.81 (t, J=15.0 Hz, 2H), 1.86 (m, 2H).
Workup
- filtrationFilter of the solid
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-fcf238dcec02406b9f092dd2581ba7ec
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07666864B2
Reaction notes
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