2-Chloronicotinonitrile → 2-(2,4,6-Trifluorophenyl)nicotinonitrile

Reaction equation

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

Participants

Reactant 2

HCID 810792-Chloronicotinonitrile

HCID 27793292,4,6-Trifluorophenylboronic Acid

Product 1

HCID 685833352-(2,4,6-Trifluorophenyl)nicotinonitrileYield 82%

Procedure

Prepared in 82% yield from 2-chloronicotinonitrile and 2,4,6-trifluorophenylboronic acid according to the procedure described for Example 153A. MS (ESI+) m/z 235.0 (M+H)+; 1H NMR (CDCl3) δ 6.83-6.88 m, 2H), 7.51 (dd, J=8.0, 4.9 Hz, 1H), 8.12 (dd, J=8.1, 1.7 Hz, 1H), 8.94 (dd, J=5.1, 1.7 Hz, 1H).

Sources & evidence

ORD record: ord-5ed2d6a6742a473b8c413010d7c2c2c5
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07704997B1

Reaction notes

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