Isopropanol → N-(3-(trifluoromethyl)benzyl)-2-(5-isopropoxy-2-nitrophenyl)isonicotinamide

HRID 625282Notes

Reaction equation

[CH3:1][CH:2]([OH:4])[CH3:3].[H-].[Na+].[F:7][C:8]([F:36])([F:35])[C:9]1[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=1)[CH2:12][NH:13][C:14](=[O:31])[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21]2[CH:26]=[C:25](F)[CH:24]=[CH:23][C:22]=2[N+:28]([O-:30])=[O:29])[CH:16]=1>CN(C)C=O.C(OCC)(=O)C>[F:7][C:8]([F:36])([F:35])[C:9]1[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=1)[CH2:12][NH:13][C:14](=[O:31])[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21]2[CH:26]=[C:25]([O:4][CH:2]([CH3:3])[CH3:1])[CH:24]=[CH:23][C:22]=2[N+:28]([O-:30])=[O:29])[CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Into a 50-mL round bottom flask, was placed a solution of propan-2-ol (2 mL) in N,N-dimethylformamide (5 mL), sodium hydride (72 mg, 3.00 mmol, 5.00 equiv), and N-(3-(trifluoromethyl)benzyl)-2-(5-fluoro-2-nitrophenyl)isonicotinamide 14d (250 mg, 0.58 mmol, 1.00 equiv, 98%). The resulting solution was stirred for 3 h at 60° C. in an oil bath. The resulting solution was diluted with 200 mL of ethyl acetate and washed with 3×30 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum to yield 280 mg (99%) of product as a brown oil.

Workup

customInto a 50-mL round bottom flask, was placed
washwashed with 3×30 mL of brine
dry with materialThe mixture was dried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-6184907204ad4c9da458bcc2040a2a15
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09301951B2

Reaction notes

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