7-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazine → 7-[4-Fluoro-3-(pyrazol-1-yl)phenyl]-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine

HRID 586335Notes

Reaction equation

HRID 586335 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:33])=[C:26]([N:28]3[CH:32]=[CH:31][CH:30]=[N:29]3)[CH:27]=2)OC1>>[F:33][C:25]1[CH:24]=[CH:23][C:22]([C:2]2[N:6]3[N:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:27][C:26]=1[N:28]1[CH:32]=[CH:31][CH:30]=[N:29]1

Participants

3

Reactant 2

HCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 223294941-[5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]-1H-pyrazole

Product 1

HCID 101547517-[4-Fluoro-3-(pyrazol-1-yl)phenyl]-3-trifluoromethylimidazo[1,2-b][1,2,4]triazineYield 39%

Procedure

7-Bromo-3-trifluoromethylimidazo[1,2-b)(1,2,4]triazine was coupled with 1-[5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]-1H-pyrazole as described in Example 3, step f, final paragraph, to give 41 mg (39%) of the title compound: 1H NMR (360 MHz, DMSO-d6) δ 6.63 (1H, t, J 2.1 Hz), 7.74 (1H, dd, J 8.7, 11.2 Hz), 8.23 (1H, ddd, J 2.1, 4.2, 8.7 Hz), 8.31 (1H, t, J 2.8 Hz), 8.71 (1H, dd, J 2.5, 7.7 Hz), 9.00 (1H, s), 9.41 (1H, s); MS (ES+) m/z 349 [M+H]+.

Sources & evidence

ORD record
ord-63a446ee3f8643fe8aa9ab7705f942e4
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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