Réaction #159451

ord-26df01bcf53045a5892c3f815b222826

Équation de réaction

O=C(O)[C@@H]1CCCN1
L-proline
CCc1ccc(Br)cc1C1C(=O)C2CCC(C2)C1=O
3-(5-Bromo-2-ethylphenyl)bicyclo[3.2.1]octane-2,4-dione
Cc1cn[nH]c1
4-methylpyrazole
O=P([O-])([O-])[O-].[K+].[K+].[K+]
potassium phosphate
→
CCc1ccc(-n2cc(C)cn2)cc1C1C(=O)C2CCC(C2)C1=O
3-[2-ethyl-5-(4-methylpyrazol-1-yl)phenyl]bicyclo-[3.2.1]octane-2,4-dione

Réactifs

O=C(O)[C@@H]1CCCN1
L-proline
CCc1ccc(Br)cc1C1C(=O)C2CCC(C2)C1=O
3-(5-Bromo-2-ethylphenyl)bicyclo[3.2.1]octane-2,4-dione
Cc1cn[nH]c1
4-methylpyrazole
O=P([O-])([O-])[O-].[K+].[K+].[K+]
potassium phosphate

Réactifs

[Cu][I]
copper (I) iodide

Solvants

CS(C)=O
DMSO

Conditions de réaction

Température
160°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    FiltrationThe mixture is filtered
  2. 2
    Autrepurified by preparative reverse-phase HPLC

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08828908B2uspto-grants-2014_09