Sodium Carbonate → 2-m-Tolyl-6-(trifluoromethyl)nicotinonitrile

HRID 1428732Notes

Reaction equation

Cl[C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:14]1([CH3:23])[CH:19]=[CH:18][CH:17]=[C:16](B(O)O)[CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].C1CCCCC1.C(OCC)(=O)C>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:14]1([CH3:23])[CH:19]=[CH:18][CH:17]=[C:16]([C:2]2[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Chloro-6-(trifluoromethyl)nicotinonitrile (3 g, 14.56 mmol) was dissolved in toluene (70 mL) and ethanol (14 mL). m-tolylboronic acid (2.969 g, 21.814 mmol), aqueous sodium carbonate solution (2 M, 14 mL) and Pd(PPh3)4 (1.684 g, 1.456 mmol) were added. The mixture was flushed with nitrogen and stirred under microwave conditions (7 bar) at 100° C. for 2 h. The concentrated reaction mixture was cooled, diluted with ethyl acetate (200 mL), passed through celite (cyclohexane/ethyl acetate 9:1, 2×1 L) and concentrated in vacuo to afford 2-m-tolyl-6-(trifluoromethyl)nicotinonitrile (1.87 g, 49%).

Workup

customThe mixture was flushed with nitrogen
customThe concentrated reaction mixture
temperaturewas cooled
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6f30511677c749ccbacfa832fd2b2618
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937092B2

Reaction notes

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