2-Methyl-2-butanol → 2-[(5-tert-butyl-2-methylphenyl)amino]-6-[4-(1H-imidazol-1-yl)piperidin-1-yl]-N,N-dimethylisonicotinamide

HRID 888998Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[CH:23]=[CH:22][N:21]=[CH:20]3)[CH2:15][CH2:14]2)[N:12]=1)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6].[C:24]([C:28]1[CH:29]=[CH:30][C:31]([CH3:35])=[C:32]([CH:34]=1)[NH2:33])([CH3:27])([CH3:26])[CH3:25].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[K+].[K+].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:24]([C:28]1[CH:29]=[CH:30][C:31]([CH3:35])=[C:32]([NH:33][C:2]2[CH:3]=[C:4]([CH:10]=[C:11]([N:13]3[CH2:18][CH2:17][CH:16]([N:19]4[CH:23]=[CH:22][N:21]=[CH:20]4)[CH2:15][CH2:14]3)[N:12]=2)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6])[CH:34]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 100 °C

Procedure

2-chloro-6-[4-(1H-imidazol-1-yl)piperidin-1-yl]-N,N-dimethylisonicotinamide (250 mg, 0.749 mmol), 5-tert-butyl-2-methylaniline (132 mg, 0.809 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (187 mg, 0.392 mmol), Pd2(dba)3 (70 mg, 0.076 mmol) and potassium carbonate (119 mg, 0.861 mmol) were combined in a vial, sealed, and put under an atmosphere of N2. Degassed t-amyl alcohol (3 ml) was added. The mixture was stirred at 100° C. overnight.

Workup

customsealed

Sources & evidence

ORD record: ord-e8625ad4e2194824b8f0841ee706d526
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252803B2

Reaction notes

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