N-methyl-2-pyrrolidone → N-(4-cyano-2-methyl-3-(trifluoromethyl)phenyl)pivalamide

HRID 2279246Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([CH3:15])[C:3]=1[C:16]([F:19])([F:18])[F:17].[CH3:20][N:21]1C(=O)CCC1>O>[C:20]([C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([CH3:15])[C:3]=1[C:16]([F:19])([F:18])[F:17])#[N:21]

Participants

Conditions

Temperature: 220 °C

Procedure

To a solution of N-(4-chloro-2-methyl-3-(trifluoromethyl)phenyl) pivalamide (3c) (0.4 g, 1.36 mmol) in NMP (5 mL) CuCN (0.3 g, 34.0 mmol) was added at room temperature under nitrogen atmosphere and heated to 220° C. for 36 h. The reaction mixture was slowly brought to room temperature, diluted with water (10 mL) and extracted with EtOAc (3×15 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude compound which was purified by column chromatography to furnish the nitrile 3d (0.2 g, 52%) as a white solid.

Workup

customwas slowly brought to room temperature
extractionextracted with EtOAc (3×15 mL)
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated under reduced pressure
customto give the crude compound which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-aea8d3a749d942af9ab8a9de16e598ac
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133182B2

Reaction notes

Loading…