5-(2-Fluorophenyl)pyridin-2(1H)-one → HCID 68014909, compound

HRID 1747795Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11](=[O:14])[NH:12][CH:13]=1.[C:15]1([N:21]2[C:25](B3OC(C)(C)C(C)(C)O3)=[CH:24][CH:23]=[N:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11](=[O:14])[N:12]([C:25]2[N:21]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:22]=[CH:23][CH:24]=2)[CH:13]=1

Participants

Conditions

Temperature: 90 °C

Procedure

5-(2-Fluorophenyl)pyridin-2(1H)-one (0.0281 g), 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.0802 g) and copper(II) acetate (0.0539 g) were suspended in pyridine (1.48 mL), and the suspension was stirred at room temperature for 12 hr and further at 90° C. for 6 hr. To the reaction mixture were added 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.0802 g) and copper(II) acetate (0.0539 g) at room temperature, and the mixture was heated under reflux for 1.5 days. The reaction mixture was cooled to room temperature, purified by NH silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/hexane to give the title compound (0.0007 g).

Workup

temperaturethe mixture was heated
temperatureunder reflux for 1.5 days
temperatureThe reaction mixture was cooled to room temperature
custompurified by NH silica gel column chromatography (ethyl acetate/hexane)
customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record: ord-6be20cb2754e4d27ae7be73d6d938390
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150588B2

Reaction notes

Loading…