2-(1-Butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)propan-2-ol → 9-fluoro-6-(1-hydroxy-1-methylethyl)benzo[c]-1,6-naphthyridin-1(2H)-one
Reaction equation
C([O:5][C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:9]=1[C:10]([C:16]([OH:19])([CH3:18])[CH3:17])=[N:11]2)CCC>Br.C(O)(=O)C>[F:24][C:22]1[CH:21]=[CH:20][C:9]2[C:10]([C:16]([OH:19])([CH3:18])[CH3:17])=[N:11][C:12]3[CH:13]=[CH:14][NH:15][C:6](=[O:5])[C:7]=3[C:8]=2[CH:23]=1Participants
Procedure
A suspension of 2-(1-butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)propan-2-ol (30 mg, 0.091 mmol) in HBr/acetic acid (33% wt) (1.0 ml) was stirred for 22 hr at room temperature. The resulting solution was concentrated to a crude oil that solidified on standing. Acetonitrile (5 ml) was added, and then concentrated to dryness in an attempt to drive off all acetic acid. The resulting solids were triturated with EtOAc (1 mL). Collection of the solids by vacuum filtration affords 9-fluoro-6-(1-hydroxy-1-methylethyl)benzo[c]-1,6-naphthyridin-1(2H)-one (HBr salt). 1H NMR (500 MHz, DMSO-D6) δ 11.90 (br d, 1H), 9.80 (dd, 1H), 9.40 (dd, 1H), 7.61-7.57 (overlapping m, 2H), 6.77 (d, 1H), 6.46 (br peak, HBr/H2O, possibly OH peak), 1.71 (s, 6H). LRMS (ESI) calc'd for (C15H13FN2O2) [M+H]+, 273.1; found 273.0.
Workup
- concentrationThe resulting solution was concentrated to a crude oil that
- additionAcetonitrile (5 ml) was added
- concentrationconcentrated to dryness in an attempt
- customThe resulting solids were triturated with EtOAc (1 mL)
- customCollection of the solids
- filtrationby vacuum filtration
Sources & evidence
- ORD record
- ord-100e009343d144a38ce004ce8cd92412
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329722B2
Reaction notes
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