2,4-Difluorophenylboronic acid → 3-(2,4-Difluorophenyl)-5-[4-fluoro-3-(pyridin-3-yl)phenyl]-[1,2,4]triazine

HRID 1064283Notes

Reaction equation

HRID 1064283 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.[F:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1B(O)O>>[F:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[C:10]1[N:11]=[N:12][CH:13]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:4]=2)[N:9]=1

Participants

3

Reactant 2

HCID 27343342,4-Difluorophenylboronic acidHCID 222735955-[4-Fluoro-3-(pyridin-3-yl)phenyl]-3-methylsulfanyl-[1,2,4]triazine

Product 1

HCID 103613953-(2,4-Difluorophenyl)-5-[4-fluoro-3-(pyridin-3-yl)phenyl]-[1,2,4]triazine

Procedure

5-[4-Fluoro-3-(pyridin-3-yl)phenyl]-3-methylsulfanyl-[1,2,4]triazine was coupled to 2,4-difluorophenylboronic acid by the method of Example 2 to give 3-(2,4-difluorophenyl)-5-[4-fluoro-3-(pyridin-3-yl)phenyl]-[1,2,4]triazine as a yellow solid: δH (400 MHz, CDCl3) 7.00-7.12 (2H, m), 7.42 (2H, m), 7.96 (1H, dd, J 2.0, 7.8 Hz), 8.27-8.36 (2H, m), 8.42 (1H, dd, J 2.5, 7.2 Hz), 8.70 (1H, s), 8.89 (1H, s), 9.66 (1H, s); m/z (ES+) 365.

Sources & evidence

ORD record
ord-ad64073a64db430ca0362432f0ef42d4
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

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