5-Bromo-N-(2-cyclohexyl-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-4-methylisoxazole-3-carboxamide → 5-Cyclohexyl-N-(2-cyclohexyl-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-4-methylisoxazole-3-carboxamide

HRID 1478180Notes

Reaction equation

Br[C:2]1[O:6][N:5]=[C:4]([C:7]([NH:9][C:10]2[C:11](=[O:23])[N:12]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[N:13]([CH3:16])[C:14]=2[CH3:15])=[O:8])[C:3]=1[CH3:24].[Br-].[CH:26]1([Zn+])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>CCOC(C)=O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:26]1([C:2]2[O:6][N:5]=[C:4]([C:7]([NH:9][C:10]3[C:11](=[O:23])[N:12]([CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)[N:13]([CH3:16])[C:14]=3[CH3:15])=[O:8])[C:3]=2[CH3:24])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 100 °C

Procedure

To 5-bromo-N-(2-cyclohexyl-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-4-methylisoxazole-3-carboxamide (75 mg, 0.189 mmol) was added cyclohexylzinc(II) bromide (0.5M in THF) (1133 μL, 0.566 mmol) and bis(tri-t-butylphosphine)palladium(0) (9.65 mg, 0.019 mmol) and the mixture was stirred at 100° C. in the microwave for 30 minutes. The resulting mixture was diluted with EtOAc and filtered and the solvent was removed under reduced pressure. The crude material was adsorbed onto silica and purification by chromatography eluting with 0-100% EtOAc in iso-hexane afforded the title compound;

Workup

filtrationfiltered
customthe solvent was removed under reduced pressure
customThe crude material was adsorbed onto silica and purification by chromatography
washeluting with 0-100% EtOAc in iso-hexane

Sources & evidence

ORD record: ord-e961c7ef316942edaf1559f17c65dbb6
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403810B2

Reaction notes

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