4-Methylpyrazole → 3-[2-Ethyl-5-(4-methylpyrazol-1-yl)phenyl]bicyclo-[3.2.1]octane-2,4-dione

HRID 72269Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:18][CH3:19])=[C:6]([CH:8]2[C:14](=[O:15])[CH:13]3[CH2:16][CH:10]([CH2:11][CH2:12]3)[C:9]2=[O:17])[CH:7]=1.[CH3:20][C:21]1[CH:22]=[N:23][NH:24][CH:25]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O>CS(C)=O.[Cu]I>[CH2:18]([C:5]1[CH:4]=[CH:3][C:2]([N:23]2[CH:22]=[C:21]([CH3:20])[CH:25]=[N:24]2)=[CH:7][C:6]=1[CH:8]1[C:14](=[O:15])[CH:13]2[CH2:16][CH:10]([CH2:11][CH2:12]2)[C:9]1=[O:17])[CH3:19]

Participants

Conditions

Temperature: 160 °C

Procedure

3-(5-Bromo-2-ethylphenyl)bicyclo[3.2.1]octane-2,4-dione (100 mg, 0.31 mmol), 4-methylpyrazole (38 mg, 0.46 mmol), potassium phosphate (264 mg, 1.24 mmol), L-proline (36 mg, 0.31 mmol) and copper (I) iodide (60 mg, 0.31 mmol) are combined in a microwave vial, suspended in DMSO and heated under microwave irradiation at 160° C. for 45 minutes. The mixture is filtered and purified by preparative reverse-phase HPLC to give 3-[2-ethyl-5-(4-methylpyrazol-1-yl)phenyl]bicyclo-[3.2.1]octane-2,4-dione.

Workup

filtrationThe mixture is filtered
custompurified by preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-26df01bcf53045a5892c3f815b222826
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828908B2

Reaction notes

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