2-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol → 2-{7-[2-Fluoro-3-(pyridin-4-yl)phenyl]imidazo[1,2-b][1,2,4]triazin-3-yl}propan-2-ol

HRID 586269Notes

Reaction equation

HRID 586269 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.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[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[C:18]1[N:22]2[N:23]=[CH:24][C:25]([C:27]([OH:30])([CH3:28])[CH3:29])=[N:26][C:21]2=[N:20][CH:19]=1

Participants

3

Reactant 2

HCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 22285310[2-Fluoro-3-(pyridin-4-yl)phenyl]boronic acid

Product 1

HCID 99463342-{7-[2-Fluoro-3-(pyridin-4-yl)phenyl]imidazo[1,2-b][1,2,4]triazin-3-yl}propan-2-ol

Procedure

2-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 70% yield by a similar procedure to that described in Example 3, step f, to afford the title compound as a yellow solid: mp 221-223° C. (CH2Cl2-EtOAc-MeOH); 1H NMR (400 MHz, DMSO-d6) δ 1.57 (6H, s), 5.79 (1H, s), 7.55 (1H, t, J 7.8 Hz), 7.66 (2H, m), 7.73 (1H, m), 8.15 (1H, m), 8.29 (1H, d, J 2.3 Hz), 8.71 (2H, m), 9.02 (1H, s); MS (ES+) m/z 350 [M+H]+. Anal. Found: C, 65.06; H, 4.62; N, 19.91%. Required for C19H16FN5O: C, 65.32; H, 4.62; N, 20.05%.

Sources & evidence

ORD record
ord-09b68a1375b64075a315a838a5d3e951
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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