(4-Methoxyphenyl)boronic acid → 5-[4-Fluoro-3-(pyridin-3-yl)phenyl]-3-(4-methoxyphenyl)-[1,2,4]triazine

HRID 1064282Notes

Reaction equation

HRID 1064282 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10](SC)[N:11]=[N:12][CH:13]=2)=[CH:4][C:3]=1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:27]3[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)[N:11]=[N:12][CH:13]=2)=[CH:4][C:3]=1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 222735955-[4-Fluoro-3-(pyridin-3-yl)phenyl]-3-methylsulfanyl-[1,2,4]triazine

Product 1

HCID 99984895-[4-Fluoro-3-(pyridin-3-yl)phenyl]-3-(4-methoxyphenyl)-[1,2,4]triazine

Procedure

5-[4-Fluoro-3-(pyridin-3-yl)phenyl]-3-methylsulfanyl-[1,2,4]triazine was coupled to 4-methoxyphenylboronic acid by the method of Example 2 to give 5-[4-fluoro-3-(pyridin-3-yl)phenyl]-3-(4-methoxyphenyl)-[1,2,4]triazine as an orange solid: δH (400 MHz, CDCl3) 7.18 (2H, dd, J 7.2, 7.2 Hz), 7.76 (1H, m), 8.27 (1H, m), 8.57 (2H, m), 8.71 (1H, m), 8.83 (1H, m), 8.98 (1H, m), 9.10 (1H, m), 9.48 (1H, m), 10.10 (1H, s); m/z (ES+) 359.

Sources & evidence

ORD record
ord-12c4f2125638492db13db595b40b5790
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

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