5-(3-Bromo-4-fluorophenyl)-3-(2,4-difluorophenyl)-[1,2,4]triazine → 5,2'-Difluoro-5'-[3-(2,4-difluorophenyl)-[1,2,4]triazin-5-yl]biphenyl-2-carbonitrile

HRID 1064277Notes

Reaction equation

HRID 1064277 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:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=1>>[F:23][C:24]1[CH:31]=[C:30]([C:2]2[CH:3]=[C:4]([C:9]3[N:10]=[C:11]([C:15]4[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=4[F:22])[N:12]=[N:13][CH:14]=3)[CH:5]=[CH:6][C:7]=2[F:8])[C:27]([C:28]#[N:29])=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 103842555-(3-Bromo-4-fluorophenyl)-3-(2,4-difluorophenyl)-[1,2,4]triazineHCID 221807884-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Product 1

HCID 104314335,2'-Difluoro-5'-[3-(2,4-difluorophenyl)-[1,2,4]triazin-5-yl]biphenyl-2-carbonitrile

Procedure

5-(3-Bromo-4-fluorophenyl)-3-(2,4-difluorophenyl)-[1,2,4]triazine was coupled to 4-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-benzonitrile by the method of Example 12 to give 5,2′-difluoro-5′-[3-(2,4-difluorophenyl)-[1,2,4]triazin-5-yl]biphenyl-2-carbonitrile as a yellow solid: δH (400 MHz, CDCl3) 6.99-7.11 (2H, m), 7.27-7.34 (2H, m), 7.47 (1H, t, J 9.4 Hz), 7.87 (1H, dd, J 5.5, 8.6 Hz), 8.30-8.41 (3H, m), 9.66 (1H, s); m/z (ES+) 407.

Sources & evidence

ORD record
ord-5639996edde74d9788856878da8b941c
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

Loading…