2-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol → HCID 10269591, compound

HRID 586275Notes

Reaction equation

HRID 586275 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([C:15]3[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=[CH:13][CH:14]=2)O1.Br[C:25]1[N:29]2[N:30]=[CH:31][C:32]([C:34]([OH:37])([CH3:36])[CH3:35])=[N:33][C:28]2=[N:27][CH:26]=1>>[OH:37][C:34]([C:32]1[CH:31]=[N:30][N:29]2[C:25]([C:9]3[CH:10]=[C:11]([C:15]4[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:12]=[CH:13][CH:14]=3)=[CH:26][N:27]=[C:28]2[N:33]=1)([CH3:36])[CH3:35]

Participants

3

Reactant 2

HCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 112436553'-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile

Product 1

HCID 10269591HCID 10269591, compoundYield 29%

Procedure

3′-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (see Example 1, step c) 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 166° C.; 1H NMR (360 MHz, CDCl3) δ 1.71 (6H, s), 3.50 (1H, br s), 7.49-7.71 (5H, m), 7.83 (1H, m), 8.10 (1H, m), 8.27 (1H, s), 8.31 (1H, m), 8.79 (1H, s); MS (ES+) m/z 356 [M+H]+.

Workup

  1. customto give a yellow solid

Sources & evidence

ORD record
ord-e59c369734df4cbf9f3a08b0c0e0bda6
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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