3-Fluoro-4-methoxyphenylboronic acid → 3-(3-Fluoro-4-methoxyphenyl)-7-hydroxy-1-naphthonitrile
Reaction equation
Br[C:2]1[CH:3]=[C:4]([C:13]#[N:14])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([OH:12])[CH:6]=2.[F:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>>[F:15][C:16]1[CH:17]=[C:18]([C:2]2[CH:3]=[C:4]([C:13]#[N:14])[C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[C:7]([OH:12])[CH:6]=3)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]Participants
3
Procedure
The title compound was prepared by reacting 3-bromo-7-hydroxy-1-naphthonitrile (0.208 g, 0.839 mmol) with 3-fluoro-4-methoxyphenylboronic acid (0.18 g, 1.1 mmol) according to method A to yield 0.16 (65%) of a light yellow solid. An analytical sample was prepared by preparative reverse phase HPLC to yield the title compound as a white solid: mp 214-216° C.; 1H NMR (DMSO-d6): δ 3.90 (3H, s), 7.23-7.32 (2H, m), 7.37 (1H, d, J=2.24 Hz), 7.65-7.70 (1H, m), 7.79 (1H, dd, J=2.22 Hz, J=13.10 Hz), 8.03 (1H, d, J=8.96 Hz), 8.41 (1H, d, J=1.86 Hz), 8.50 (1H, d, J=1.43 Hz), 10.55 (1H, s); MS (ESI) m/z292 (M−H)−.
Sources & evidence
- ORD record
- ord-4ebee11452804ad28a768e6f95a59cd1
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06914074B2
Reaction notes
Loading…