Pyridine → HCID 22025365, compound

HRID 1792830Notes

Reaction equation

[O:1]([C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:17]1[CH:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:18]1.N1C=CC=CC=1>C1COCC1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:25]([O:24][C:22]([C:19]1[N:18]([C:11]2[CH:12]=[CH:13][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)[N:17]=[CH:21][CH:20]=1)=[O:23])[CH3:26].[CH2:25]([O:24][C:22]([C:19]1[CH:20]=[CH:21][N:17]([C:11]2[CH:12]=[CH:13][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)[N:18]=1)=[O:23])[CH3:26]

Participants

Conditions

Temperature: 200 °C

Procedure

To a suspension of 4-phenoxyphenylboronic acid (1.70 g, 7.85 mmol), ethyl 3-pyrazolecarboxylate (0.55 g, 3.92 mmol), copper(II)acetate (1.1 g, 5.89 mmol) and 4 Å molecular sieves (powdered and heated at 200° C. for 2 h prior to use) in 30 mL of anhydrous THF was added 0.6 mL of pyridine. The reaction was stirred open to air at room temperature for 2 days and then filtered and the filtrate was concentrated to dryness. The crude product was purified by flash chromatography, eluting with 15% EtOAc/hexane, affording 5-ethoxycarbonyl-1-(4-phenoxyphenyl)-1H-pyrazole (Rf=0.6, 55 mg, 4.6%) and 3-ethoxycarbonyl-1-(4-phenoxyphenyl)-1H-pyrazole (Rf=0.5, 125 mg, 10.3%).

Workup

filtrationfiltered
concentrationthe filtrate was concentrated to dryness
customThe crude product was purified by flash chromatography
washeluting with 15% EtOAc/hexane

Sources & evidence

ORD record: ord-677e608584e14eae9651397497b27789
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07078426B2

Reaction notes

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