Acetic Acid Mixture with Hydrobromic Acid → HCID 59375658, compound
Reaction equation
C([O:5][C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:16]([CH3:18])=[CH2:17])=[N:11]2)CCC.[BrH:24].C(O)(=O)C>>[Br:24][CH2:17][CH:16]([C:10]1[C:9]2[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:8]=2[C:7]2[C:6](=[O:5])[NH:15][CH:14]=[CH:13][C:12]=2[N:11]=1)[CH3:18]Participants
3
Procedure
A solution of 1-butoxy-9-fluoro-6-isopropenylbenzo[c]-1,6-naphthyridine (26 mg, 0.063 mmol) in HBr/acetic acid (33% wt) (1.0 ml) was stirred for 18 hr at room temperature. The reaction mixture was concentrated to a crude solid that was taken up into acetonitrile (5 mL) and concentrated again in an attempt to drive off more acetic acid. The resulting solid was triturated with EtOAc (1 mL), then collected by vacuum filtration to afford 6-(2-bromo-1-methylethyl)-9-fluorobenzo[c]-1,6-naphthyridin-1(2H)-one (HBr salt). LRMS (ESI) calc'd for (C15H12BrFN2O) [M+H]+, 335.0; found 335.0.
Workup
- concentrationThe reaction mixture was concentrated to a crude solid that
- concentrationconcentrated again in an attempt