Pyridine → HCID 66616142, compound

HRID 2172150Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[C:9]#[N:10])=[N:2]1.[F:14][CH:15]([F:26])[O:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.N1C=CC=CC=1>CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:14][CH:15]([F:26])[O:16][C:17]1[CH:22]=[CH:21][C:20]([N:1]2[CH:5]=[CH:4][C:3]([C:6]3[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=3)[C:9]#[N:10])=[N:2]2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 35 °C

Procedure

A solution of 3-(1H-pyrazol-3-yl)-benzonitrile (400 mg, 2.36 mmol) and 4-difluoromethoxybenzeneboronic acid (1.02 g, 5.44 mmol) in dimethylformamide (20 mL) is treated with copper (II) acetate (472 mg), pyridine (0.36 mL), and powdered, activated 4 Å molecular sieves (1 g). The resulting mixture is heated to 35° C. for 3 h, cooled and partially evaporated. The residue is partitioned between 1 M aq. HCl and ethyl acetate (200 mL each), and the extract is washed with brine (100 mL), dried over MgSO4, filtered and evaporated. The residue is separated by column chromatography (silica gel, 1:1 CH2Cl2-hexane) to afford 3-[1-(4-difluoromethoxy-phenyl)-1H-pyrazol-3-yl]-benzonitrile (200 mg, 23%).

Workup

temperaturecooled
custompartially evaporated
customThe residue is partitioned between 1 M aq. HCl and ethyl acetate (200 mL each)
washthe extract is washed with brine (100 mL)
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customThe residue is separated by column chromatography (silica gel, 1:1 CH2Cl2-hexane)

Sources & evidence

ORD record: ord-98a55757933a4a9ea5c8ba6639f2f0e5
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051342B2

Reaction notes

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