Tetrahydrofuran → (4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone

HRID 928804Notes

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])[N:17]=[N:16][CH:15]=3)[OH:13])[CH:10]=2)[N:5]=[C:4]([O:20][CH3:21])[C:3]=1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1.O1CCOCC1.C1COCC1.[Al]>O=[Mn]=O.CCOCC>[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])[N:17]=[N:16][CH:15]=3)=[O:13])[CH:10]=2)[N:5]=[C:4]([O:20][CH3:21])[C:3]=1[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a 100 mL flask containing (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol (745 mg, 1.61 mmol, Intermediate 50: step b) was added 1,4-dioxane (36 mL) and THF (11 mL) to give a suspension at room temperature. Heating to approximately 45° C. formed a homogeneous solution. Then, activated MnO2 (719 mg, 8.3 mmol) was introduced and the mixture was heated to 80° C. in an aluminum heating mantle under an atmosphere of N2. After 2 hours, the mixture was filtered through a Celite® pad, rinsed with THF and concentrated to give a white solid. Trituration from Et2O gave the title compound as a white solid.

Workup

customto give a suspension at room temperature
customformed a homogeneous solution
filtrationthe mixture was filtered through a Celite® pad
washrinsed with THF
concentrationconcentrated
customto give a white solid

Sources & evidence

ORD record: ord-fff8a33d61da4574bcbd60b41f3afb53
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290476B2

Reaction notes

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