N-[1-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]-2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]pent-4-enamide → N-[1-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]-3-methyl-1-(trifluoromethyl)-5,6-dihydroimidazo[1,5-a]pyridine-5-carboxamide

HRID 1754375Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]([CH3:15])[CH3:14])=[C:11]([NH:16][C:17](=[O:34])[CH:18]([N:22]3[C:26]([CH:27]=[CH2:28])=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]=[C:23]3[CH3:33])[CH2:19]C=C)[CH:10]=[N:9]2)=[CH:4][CH:3]=1>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]([CH3:15])[CH3:14])=[C:11]([NH:16][C:17]([CH:18]3[N:22]4[C:23]([CH3:33])=[N:24][C:25]([C:29]([F:30])([F:32])[F:31])=[C:26]4[CH:27]=[CH:28][CH2:19]3)=[O:34])[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To N-[1-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]-2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]pent-4-enamide (147 mg, 0.298 mmol) was added CH2Cl2 (10 mL) and benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (Grubb's first generation catalyst, 122.6 mg, 0.149 mmol), and the resulting mixture was stirred at 45° C. for 3 h. The reaction mixture was then directly adsorbed on SiO2 and purified by flash chromatography (SiO2, 80% EtOAc/hexanes) to furnish N-[1-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]-3-methyl-1-(trifluoromethyl)-5,6-dihydroimidazo[1,5-a]pyridine-5-carboxamide (30 mg, 0.064 mmol, 22% yield).

Workup

custompurified by flash chromatography (SiO2, 80% EtOAc/hexanes)

Sources & evidence

ORD record: ord-18ca35a549c34244be4bc9472a981b99
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169248B2

Reaction notes

Loading…