2-Chloronicotinonitrile → 2-(4-Fluoro-2-methoxyphenyl)nicotinonitrile

HRID 1512329Notes

Reaction equation

HRID 1512329 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]=[CH:15][C:14](B(O)O)=[C:13]([O:20][CH3:21])[CH:12]=1>>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[N:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[C:13]([O:20][CH3:21])[CH:12]=1

Participants

3

Reactant 2

HCID 810792-ChloronicotinonitrileHCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acid

Product 1

HCID 685820932-(4-Fluoro-2-methoxyphenyl)nicotinonitrileYield 85%

Procedure

Prepared in 85% yield from 2-chloronicotinonitrile and 4-fluoro-2-methoxyphenylboronic acid according to the procedure described for Example 153A. MS (ESI−) m/z 228.9 (M+H)+; 1H NMR (CDCl3) δ 6.75-6.84 (m, 2H), 7.37 (dd, J=8.0, 4.9 Hz, 1H), 7.44 (dd, J=8.5, 6.8 Hz, 1H), 8.02 (dd, J=7.8, 1.7 Hz, 1H), 8.86 (dd, J=4.9, 1.9 Hz, 1H).

Sources & evidence

ORD record
ord-0cf433de2b694a2db1866e33d714c144
Source dataset
uspto-grants-2012_07
Patent number
US08217067B2

Reaction notes

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