2-Methyl-2-butanol → 4-[(4-cyano-1-phenyl-1H-pyrazol-3-yl)amino]-N,N-dimethylbenzamide

HRID 1961508Notes

Reaction equation

[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.Br[C:16]1[CH:26]=[CH:25][C:19]([C:20]([N:22]([CH3:24])[CH3:23])=[O:21])=[CH:18][CH:17]=1.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.C(O)(CC)(C)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]>[C:7]([C:6]1[C:2]([NH:1][C:16]2[CH:26]=[CH:25][C:19]([C:20]([N:22]([CH3:24])[CH3:23])=[O:21])=[CH:18][CH:17]=2)=[N:3][N:4]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=1)#[N:8]

Participants

Conditions

Temperature: 100 °C

Procedure

3-amino-1-phenyl-1H-pyrazole-4-carbonitrile (60 mg, 0.326 mmol), 4-bromo-N,N-dimethylbenzamide (74.3 mg, 0.326 mmol), Pd2 dba3 (14.91 mg, 0.016 mmol), K2CO3 (49.5 mg, 0.358 mmol) and X-Phos (38.8 mg, 0.081 mmol) were added to a 5 mL microwave vial. Tert-amyl alcohol (1 mL) was added and the vial was evacuated and back-filled with N2 (×3). The resulting mixture was stirred at 100° C. overnight. Room temperature was attained, EtOAc was added and the solvent removed in vacuo while loading onto silica. Purification of the residue by MPLC (0-10% MeOH—CHCl3) followed by MPLC (12-100% EtOAc-hexanes) gave 4-[(4-cyano-1-phenyl-1H-pyrazol-3-yl)amino]-N,N-dimethylbenzamide as a pale yellow solid.

Workup

customthe vial was evacuated
additionback-filled with N2 (×3)
customRoom temperature
additionEtOAc was added
customthe solvent removed in vacuo
customPurification of the residue by MPLC (0-10% MeOH—CHCl3)

Sources & evidence

ORD record: ord-34d8ab73bdbd4b0898550ecaa4c7ce16
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415346B2

Reaction notes

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