Phenol → 3-(3-Fluoro-4-methoxy-phenyl)-6-phenoxy-pyridazine

HRID 1993367Notes

Reaction equation

Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([F:16])[CH:9]=2)=[CH:6][CH:7]=1.[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[F:16][C:10]1[CH:9]=[C:8]([C:5]2[N:4]=[N:3][C:2]([O:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:7][CH:6]=2)[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 3-chloro-6-(3-fluoro-4-methoxy-phenyl)-pyridazine (1.0 g, 4019 mmol), phenol (0.26 g, 5.03 mmol) and Cs2CO3 (1.64 g, 5.03 mmol) in 15 mL of DMF (in microwave tube) was heated in a microwave (Personal Chemistry, Emrys Optimizer) at 150° C. for 15 min. The mixture was cooled to RT and diluted with 60 mL of EtOAc. The solution was washed with 20 mL of satd. NaHCO3 followed by 20 mL of brine, dried over Na2SO4 and concentrated in vacuo. The solid was washed with 50% EtOAc/hexanes to provide the title compound as an off-white solid. MS (ESI pos. ion) m/z: 297.3 (M+H). Calc'd Exact Mass for C17H13FN2O2: 296.30.

Workup

temperatureThe mixture was cooled to RT
washThe solution was washed with 20 mL of satd
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
washThe solid was washed with 50% EtOAc/hexanes

Sources & evidence

ORD record: ord-925058e3e1864a10aeeacdf2e0ac1a6f
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652009B2

Reaction notes

Loading…