Pyrrolidine → 5-Fluoro-2-(3-pyrrolidin-1-ylmethyl-benzo[d]isoxazol-6-yloxy)-benzonitrile
Reaction equation
Br[CH2:2][C:3]1[C:7]2[CH:8]=[CH:9][C:10]([O:12][C:13]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:14]=3[C:15]#[N:16])=[CH:11][C:6]=2[O:5][N:4]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>ClCCl>[F:21][C:18]1[CH:19]=[CH:20][C:13]([O:12][C:10]2[CH:9]=[CH:8][C:7]3[C:3]([CH2:2][N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)=[N:4][O:5][C:6]=3[CH:11]=2)=[C:14]([CH:17]=1)[C:15]#[N:16]Participants
4
Procedure
2-(3-Bromomethylbenzo[d]isoxazol-6-yloxy)-5-fluorobenzonitrile (4v) (0.295 g, 0.850 mmol) was dissolved in dichloromethane and pyrrolidine was added dropwise (0.18 g, 2.5 mmol). After 2 hours, the reaction was concentrated and partitioned between NaHCO3 (15 mL) and EtOAc (30 mL). The aqueous layer was back extracted with EtOAc and the organic fractions were combined, washed with brine and dried (MgSO4) to provide compound (5v) (0.27 g, 94%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.90 (d, J=8.6 Hz, 1H), 7.42 (d, J=6.3 Hz, 1H), 7.30-7.26 (m, 1H), 7.11 (s, 1H), 7.07-7.02 (m, 2H), 4.02 (s, 2H), 2.62 (s, 4H), 1.82 (s, 4H); MS (ESI+) m/z 338 (M+H) detected.