2-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol → 2'-Fluoro-5'-[3-(1-hydroxy-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]biphenyl-2-carbonitrile

HRID 586262Notes

Reaction equation

HRID 586262 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][C:3]=1[C:17]1[C:18]([C:23]#[N:24])=[CH:19][CH:20]=[CH:21][CH:22]=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:7]=[CH:6][C:5]([C:26]2[N:30]3[N:31]=[CH:32][C:33]([C:35]([OH:38])([CH3:36])[CH3:37])=[N:34][C:29]3=[N:28][CH:27]=2)=[CH:4][C:3]=1[C:17]1[C:18]([C:23]#[N:24])=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 117716472′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile

Product 1

HCID 99477182'-Fluoro-5'-[3-(1-hydroxy-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]biphenyl-2-carbonitrileYield 29%

Procedure

2′-Fluoro-5′-(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 29% yield using a similar procedure to that described in Example 3, step f, to give a yellow solid: mp 187° C.; 1H NMR (360 MHz, CDCl3) δ 1.71 (6H, s), 3.25 (1H, br s), 7.36-7.84 (5H, m), 8.09-8.16 (2H, m), 8.26 (1H, s), 8.76 (1H, s); MS (ES+) m/z 374 [M+H]+. Anal. Found: C, 67.34; H, 4.30, N. 18.47%. Required for C21H16FN5O: C, 67.55; H, 4.32; N, 18.76%.

Workup

  1. customto give a yellow solid

Sources & evidence

ORD record
ord-3ca634692ec4438ab271152b3c98782f
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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