Dichloromethane → HCID 118006240, compound

HRID 926485Notes

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]([CH2:21][CH3:22])[C:3]=1[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1.ClCCl>O1CCOCC1.[O-2].[O-2].[Mn+4]>[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]([CH2:21][CH3:22])[C:3]=1[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:31])[F:33])=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture containing (4-chloro-2-ethyl-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanol (325 mg, 0.601 mmol, Intermediate 25: step a) and manganese dioxide (308 mg, 3.01 mmol) in dioxane (3 mL) was heated to 100° C. After 2 hours, the mixture was cooled to 23° C. Dichloromethane (20 mL) was added and the mixture was filtered through Celite®, rinsing with dichloromethane. Silica gel (5 g) was added to the filtrate and the solvent was removed by rotary evaporation to afford a free-flowing powder. The powder was loaded onto a column of silica gel for purification. Elution with hexanes-ethyl acetate provided the title compound as an off-white solid.

Workup

filtrationthe mixture was filtered through Celite®
washrinsing with dichloromethane
additionSilica gel (5 g) was added to the filtrate
customthe solvent was removed by rotary evaporation
customto afford a free-flowing powder
customThe powder was loaded onto a column of silica gel for purification
washElution with hexanes-ethyl acetate

Sources & evidence

ORD record: ord-48e09d86c14f4ea1a7c149ebe08eeb83
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284308B2

Reaction notes

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