Nitrogen → (4-Chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone

HRID 926518Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([C:14]3[N:18]([CH3:19])[C:17]([CH3:20])=[N:16][CH:15]=3)[OH:13])[CH:10]=2)[N:5]=[C:4]([O:21][CH3:22])[C:3]=1[CH2:23][C:24]1[CH:25]=[N:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=1.O1CCOCC1.N#N>O=[Mn]=O.C1COCC1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:14]3[N:18]([CH3:19])[C:17]([CH3:20])=[N:16][CH:15]=3)=[O:13])[CH:10]=2)[N:5]=[C:4]([O:21][CH3:22])[C:3]=1[CH2:23][C:24]1[CH:25]=[N:26][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 80 °C

Procedure

(4-Chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanol (0.552 g, 1.158 mmol, Intermediate 45: step e), 1,4-dioxane (25 mL), dry THF (3 mL) and activated MnO2 (0.503 g, 5.788 mmol) were combined in a round-bottom flask and the mixture was heated at 80° C. under a condenser and a positive pressure of N2 overnight. The reaction was allowed to cool to ambient temperature and was filtered through Celite®, rinsing with THF. The filtrate was concentrated to provide the title compound which was used without further purification.

Workup

temperatureto cool to ambient temperature
filtrationwas filtered through Celite®
washrinsing with THF
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-ae845bb65ca04f2088b4e665ec3a8339
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284308B2

Reaction notes

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