7-(2-Chloropyridin-4-yl)-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine → 5-Fluoro-2-[4-(3-trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)pyridin-2-yl]benzonitrile

HRID 347698Notes

Reaction equation

HRID 347698 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:12]3[N:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[N:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[F:21][C:22]1[CH:23]=[CH:24][C:25](B2OC(C)(C)C(C)(C)O2)=[C:26]([CH:29]=1)[C:27]#[N:28]>>[F:21][C:22]1[CH:23]=[CH:24][C:25]([C:2]2[CH:7]=[C:6]([C:8]3[N:12]4[N:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[N:16][C:11]4=[N:10][CH:9]=3)[CH:5]=[CH:4][N:3]=2)=[C:26]([CH:29]=1)[C:27]#[N:28]

Participants

3

Reactant 2

HCID 113355617-(2-Chloropyridin-4-yl)-3-trifluoromethylimidazo[1,2-b][1,2,4]triazineHCID 221807905-Fluoro-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Product 1

HCID 102494205-Fluoro-2-[4-(3-trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)pyridin-2-yl]benzonitrileYield 24%

Procedure

7-(2-Chloropyridin-4-yl)-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine was reacted with 5-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile by a similar procedure to that described in Example 1, step g, to give the title compound in 24% yield: 1H NMR (400 MHz, CD Cl3) δ 7.48 (1H, ddd, J 2.7, 7.8, 8.6), 7.57 (1H, dd, J 2.7, 8.2), 8.01 (1H, dd, J 5.3, 8.8), 8.08 (1H, dd, J 1.8, 5.3), 8.63 (1H, dd, J 1.0, 1.8), 8.82 (1H, s), 8.92 (1H, s), 8.95 (1H, dd, J 1.0, 5.3).

Sources & evidence

ORD record
ord-ccd3bc82b7d3471da78cf520eb6e84b2
Source dataset
uspto-grants-2007_02
Patent number
US07176203B2

Reaction notes

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