7-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazine → 5,2'-Difluoro-5'-(3-trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)biphenyl-2-carbonitrile

HRID 2121377Notes

Reaction equation

HRID 2121377 reaction equation
Br[C:2]1[N:6]2[N:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]2=[N:4][CH:3]=1.CC1(C)COB([C:22]2[CH:23]=[CH:24][C:25]([F:37])=[C:26]([C:28]3[C:29]([C:35]#[N:36])=[CH:30][CH:31]=[C:32]([F:34])[CH:33]=3)[CH:27]=2)OC1>>[F:34][C:32]1[CH:33]=[C:28]([C:26]2[CH:27]=[C:22]([C:2]3[N:6]4[N:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]4=[N:4][CH:3]=3)[CH:23]=[CH:24][C:25]=2[F:37])[C:29]([C:35]#[N:36])=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 116884435'-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-5,2'-difluorobiphenyl-2-carbonitrile

Product 1

HCID 101578525,2'-Difluoro-5'-(3-trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)biphenyl-2-carbonitrileYield 46%

Procedure

7-Bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine was coupled with 5′-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-5,2′-difluorobiphenyl-2-carbonitrile as described in Example C to give 68.7 mg (46%) of 5,2′-difluoro-5′-(3-trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)biphenyl-2-carbonitrile as a yellow solid: mp 200-201° C.; 1H NMR (360 MHz, CDCl3) δ7.25-7.34 (2H, m), 7.44 (1H, t, J8.9 Hz), 7.87 (1H, dd, J5.4, 8.6 Hz), 8.18-8.26 (2H, m), 8.63 (1H, s), 8.82 (1H, s); MS (ES+) m/z 401. Anal. Found: C, 55.98; H, 2.13; N, 17.49%. Required for C19H8F5N5.0.3H2O: C, 56.11; H, 2.13; N, 17.22%.

Sources & evidence

ORD record
ord-c1fbfea57667413da69732b98df82f48
Source dataset
uspto-grants-2004_02
Patent number
US06696444B2

Reaction notes

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