Potassium Carbonate → 3-[[4-(Methylsulfonyl)phenyl]amino]-1-phenyl-1H-pyrazole-4-carboxamide

HRID 1961502

Reaktionsgleichung

[NH2:1][C:2]1[C:6]([C:7]([NH2:9])=[O:8])=[CH:5][N:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1.[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1)(=[O:19])=[O:18].C([O-])([O-])=O.[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CCO>[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:1][C:2]2[C:6]([C:7]([NH2:9])=[O:8])=[CH:5][N:4]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:3]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

3-amino-1-phenyl-1H-pyrazole-4-carboxamide (50 mg, 0.247 mmol), 4-bromophenyl methyl sulfone (58.1 mg, 0.247 mmol), Pd2 dba3 (22.64 mg, 0.025 mmol), K2CO3 (37.6 mg, 0.272 mmol) and X-Phos (58.9 mg, 0.124 mmol) were added to a 5 mL microwave vial. Degassed EtOH (0.75 mL) was added and the vial evacuated and back-filled with N2 (×3). The resulting mixture was stirred at 100° C. for 4 hours. Room temperature was attained, MeOH was added and the solvent removed in vacuo while loading onto silica. Purification of the residue by MPLC (0-6% MeOH—CHCl3) gave 3-{[4-(methylsulfonyl)phenyl]amino}-1-phenyl-1H-pyrazole-4-carboxamide as a pale yellow solid after triturating in DCM.

Aufarbeitung

customthe vial evacuated
additionback-filled with N2 (×3)
customRoom temperature
additionMeOH was added
customthe solvent removed in vacuo
customPurification of the residue by MPLC (0-6% MeOH—CHCl3)

Quellen und Nachweise

ORD-Eintrag: ord-35ec93f96f584bbd9103b8af9f73aa1d
Quelldatensatz: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08415346B2

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