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

HRID 586242Notes

Reaction equation

HRID 586242 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.[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25](B(O)O)[C:24]=1[F:32])#[N:16]>>[F:32][C:24]1[C:25]([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:26][CH:27]=[CH:28][C:23]=1[C:18]1[C:17]([C:15]#[N:16])=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 11644397(2'-Cyano-2-fluoro-[1,1'-biphenyl]-3-yl)boronic acid

Product 1

HCID 101567802'-Fluoro-3'-(3-trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)biphenyl-2-carbonitrileYield 15%

Procedure

7-Bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine was coupled with 2′-cyano-2-fluorobiphenyl-3-boronic acid as described in Example 3, step f, to give 21 mg (15%) of the title compound: mp 167-168° C.; 1H NMR (360 MHz, CDCl3) δ 7.47-7.60 (4H, m), 7.73 (1H, dd, J 1.4, 7.7 Hz), 7.84 (1H, dd, J 0.7, 7.0 Hz), 8.26-8.30 (1H, m), 8.69 (1H, d, J 2.8 Hz), 8.83 (1H, s); MS (ES+) m/z 384 [M+H]+. Anal. Found: C, 59.14; H, 2.75; N, 18.01%. Required for C19H9F4N5.0.2H2O: C, 58.98; H, 2.45; N, 18.10%.

Sources & evidence

ORD record
ord-125bc075e6cc4c6c80458e941c702f4d
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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