HCID 11459593, compound → 3'-[3-(1-Fluoro-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]-4,2',6'-trifluorobiphenyl-2-carbonitrile

HRID 891856Notes

Reaction equation

HRID 891856 reaction equation
CC1(C)C(C)(C)OB([C:9]2[C:10]([F:25])=[C:11]([C:16]3[C:17]([C:23]#[N:24])=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:12]([F:15])=[CH:13][CH:14]=2)O1.Br[C:28]1[N:32]2[N:33]=[CH:34][C:35]([C:37]([F:40])([CH3:39])[CH3:38])=[N:36][C:31]2=[N:30][CH:29]=1>>[F:40][C:37]([C:35]1[CH:34]=[N:33][N:32]2[C:28]([C:9]3[C:10]([F:25])=[C:11]([C:16]4[C:17]([C:23]#[N:24])=[CH:18][C:19]([F:22])=[CH:20][CH:21]=4)[C:12]([F:15])=[CH:13][CH:14]=3)=[CH:29][N:30]=[C:31]2[N:36]=1)([CH3:39])[CH3:38]

Participants

3

Reactant 2

HCID 11459593HCID 11459593, compoundHCID 222400873'-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-4,2',6'-trifluorobiphenyl-2-carbonitrile

Product 1

HCID 222400823'-[3-(1-Fluoro-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]-4,2',6'-trifluorobiphenyl-2-carbonitrileYield 38%

Procedure

3′-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-4,2′,6′-trifluorobiphenyl-2-carbonitrile was reacted with 7-bromo-3-(1-fluoro-1-methylethyl)imidazo[1,2-b][1,2,4]triazine by a similar procedure to that described in Example 2, step e, to give the title compound in 38% yield as a yellow solid: mp 166-169° C. (EtOAc-isohexane); 1H NMR (360 MHz, CDCl3) δ 1.85 (6H, d, J 22.1); 7.25 (1H, td, J 8.6, 1.4), 7.46 (1H, td, J 8.6, 2.7), 7.54–7.59 (2H, m), 8.30 (1H, dt, J 8.3, 6.2), 8.35 (1H, d, J 3.0), 8.80 (1H, d, J 1.2); MS (ES+) m/z 412 [M+H]+. Anal. Found: C, 61.34; H, 3.29; N, 16.72%. Required for C21H13F4N5.0.05C4H8O2: C, 61.24; H, 3.25; N, 16.84%.

Sources & evidence

ORD record
ord-b7094bfcd3494e24a3810e79b2a26990
Source dataset
uspto-grants-2006_02
Patent number
US07005431B2

Reaction notes

Loading…