2-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol → HCID 10154824, compound

HRID 586261Notes

Reaction equation

HRID 586261 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.Br[C:18]1[N:22]2[N:23]=[CH:24][C:25]([C:27]([OH:30])([CH3:29])[CH3:28])=[N:26][C:21]2=[N:20][CH:19]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]2[N:22]3[N:23]=[CH:24][C:25]([C:27]([OH:30])([CH3:28])[CH3:29])=[N:26][C:21]3=[N:20][CH:19]=2)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 22285265HCID 22285265, compound

Product 1

HCID 10154824HCID 10154824, compound

Procedure

4-Fluoro-3-(pyridin-4-yl)benzeneboronic acid was coupled with 2-(7-bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol in 80% yield by a similar procedure to that described in Example 3, step f, to afford the title compound as a yellow solid: mp 233-237° C. (CH2Cl2-EtOAc-MeOH); 1H NMR (400 MHz, DMSO-d6) δ 1.57 (6H, s), 5.78 (1H, s), 7.60 (1H, dd, J 11.0, 8.6 Hz), 7.68-7.70 (2H, m), 8.27 (1H, m), 8.35 (1H, dd, J 7.4, 2.3 Hz), 8.53 (1H, s), 8.73 (2H, m), 9.04 (1H, s); MS (ES+) m/z 350 [M+H]+. Anal. Found: C, 64.87; H, 4.58; N, 19.79%. Required for C19H16FN5O.0.1H2O: C, 64.98; H, 4.65; N, 19.94%.

Sources & evidence

ORD record
ord-b386a6103b2b40d5b5bd57d6941ca071
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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