Selectfluor → 6-(2-fluoro-3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine
Reaction equation
[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+]([F:21])(CC2)C1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([C:32]2[N:37]=[CH:36][C:35]3[C:38]([I:47])=[N:39][N:40]([CH:41]4[CH2:46][CH2:45][CH2:44][CH2:43][O:42]4)[C:34]=3[CH:33]=2)[CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1>C(#N)C>[F:21][C:25]1[C:24]([O:23][CH3:22])=[CH:29][C:28]([O:30][CH3:31])=[CH:27][C:26]=1[C:32]1[N:37]=[CH:36][C:35]2[C:38]([I:47])=[N:39][N:40]([CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][O:42]3)[C:34]=2[CH:33]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate (0.84 g, 2.4 mmol) (Alfa Aesar Cat. No. L17003) was added to a stirring solution of 6-(3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine (0.55 g, 1.2 mmol) in acetonitrile (15 mL). The mixture was stirred at r.t. for 1 h. The solid was filtered out. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.52 g) which contained some amount of the corresponding di-fluoride analogue, and was directly used in next step reaction without further purification. LCMS (M+H)+=484.0
Workup
- filtrationThe solid was filtered out
- concentrationThe filtrate was concentrated under reduced pressure
- customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)
Sources & evidence
- ORD record
- ord-2be5ea6d829f47d28912c6ff51841c69
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266892B2
Reaction notes
Loading…