2-Fluorophenylboronic acid → 5-(2,2'-Difluorobiphenyl-5-yl)-3-(2,4-difluorophenyl)-[1,2,4]triazine

HRID 1064276Notes

Reaction equation

HRID 1064276 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=3[F:22])[N:12]=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O>>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=3[F:22])[N:12]=[N:13][CH:14]=2)=[CH:3][C:2]=1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[F:23]

Participants

3

Reactant 2

HCID 27343542-Fluorophenylboronic acidHCID 103842555-(3-Bromo-4-fluorophenyl)-3-(2,4-difluorophenyl)-[1,2,4]triazine

Product 1

HCID 103397955-(2,2'-Difluorobiphenyl-5-yl)-3-(2,4-difluorophenyl)-[1,2,4]triazine

Procedure

5-(3-Bromo-4-fluorophenyl)-3-(2,4-difluorophenyl)-[1,2,4]triazine was coupled to 2-fluorophenylboronic acid by the method of Example 12 to give 5-(2,2′-difluorobiphenyl-5-yl)-3-(2,4-difluorophenyl)-[1,2,4]triazine as a fluffy yellow solid: δH (400 MHz, CDCl3) 6.99-7.10 (2H, m), 7.21-7.23 (1H, m), 7.27-7.31 (1H, m), 7.37-7.48 (3H, m), 8.29-8.35 (3H, m), 9.64 (1H, s); m/z (ES+) 382.

Sources & evidence

ORD record
ord-d86419457e964098ba29ca1f430548b3
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

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