2-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol → 4-Fluoro-3'-[3-(1-hydroxy-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]-biphenyl-2-carbonitrile

HRID 1167131Notes

Reaction equation

HRID 1167131 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:23]#[N:24])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10](B3OC(C)(C)C(C)(C)O3)[CH:9]=2)=[CH:6][CH:7]=1.Br[C:26]1[N:30]2[N:31]=[CH:32][C:33]([C:35]([OH:38])([CH3:37])[CH3:36])=[N:34][C:29]2=[N:28][CH:27]=1>>[F:1][C:2]1[CH:3]=[C:4]([C:23]#[N:24])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:26]3[N:30]4[N:31]=[CH:32][C:33]([C:35]([OH:38])([CH3:36])[CH3:37])=[N:34][C:29]4=[N:28][CH:27]=3)[CH:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 222853364-Fluoro-3'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile

Product 1

HCID 102706684-Fluoro-3'-[3-(1-hydroxy-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]-biphenyl-2-carbonitrile

Procedure

4- Fluoro-3′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile was coupled to 2-(7-bromoimidazo[1,2-b][1,2,4]triazin-3-yl)-propan-2-ol in 32% yield using a similar procedure to that described in Example C, step f, to give a yellow solid: mp 175° C.; 1H NMR (360 MHz, CDCl3) δ 1.71 (6H, s), 3.25 (1H, br s), 7.41-7.67 (5H, m), 8.01 (1H, m), 8.24 (1H, s), 8.31 (1H, s), 8.78 (1H, s); MS (ES+) m/z 374 [M+H]+. Anal. Found: C, 67.38; H, 4.27; N, 18.51%. Required for C21H16FN5O: C, 67.55; H, 4.32; N, 18.76%.

Workup

  1. customto give a yellow solid

Sources & evidence

ORD record
ord-4f51036a14b64dd9b2336da74da4a200
Source dataset
uspto-grants-2003_09
Patent number
US06617326B2

Reaction notes

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