Methyl 8-chloro-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylate → Methyl 8-chloro-7-fluoro-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylate
反応式
[Cl:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[C:4](=[O:16])[CH:3]=1.[B-](F)(F)(F)[F:18].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CN(C=O)C>[Cl:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[C:4](=[O:16])[C:3]=1[F:18]参加物
4
実験手順
Methyl 8-chloro-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylate (7b, 1.23 g, 5.1 mmol, 1 eq) was dissolved in DMF (10 ml) at 88° C. Selectfluor (3.61 g, 10.2 mmol, 2 eq) in DMF (10 ml) was added drop wise and the mixture heated for 2 hours. After concentration in vacuo the residue was purified by flash chromatography using 20-70% EtOAc/Hexane as eluent to give the title compound as an off-white solid (600 mg, 45%). [M+H] calc'd for C11H11ClFNO3, 260. found, 260