2-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol → HCID 9968257, compound

HRID 586294Notes

Reaction equation

HRID 586294 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][N: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][N:12]=1

Participants

3

Reactant 2

HCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 22285299HCID 22285299, compound

Product 1

HCID 9968257HCID 9968257, compound

Procedure

4-Fluoro-3-(pyrimidin-4-yl)phenylboronic acid (50 mg, 0.23 mmol) was coupled to 2-(7-bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol (56 mg, 0.22 mmol) using the method of Example 20. Purification by chromatography (silica gel, 3% MeOH/CH2Cl2) then recrystallisation from hot toluene gave the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 1.57 (6H, s), 5.77 (1H, s), 7.62 (1H, dd, J 11, 9 Hz), 7.98-8.01 (1H, m), 8.28-8.33 (1H, m), 8.49 (1H, s), 8.80 (1H, dd, J 7, 2 Hz), 8.97 (1H, d, J 5 Hz), 9.05 (1H, s), 9.38 (1H, d, J 1 Hz); MS (ES+) m/z 351 [M+H]+.

Workup

  1. customPurification by chromatography (silica gel, 3% MeOH/CH2Cl2)
  2. customrecrystallisation from hot toluene

Sources & evidence

ORD record
ord-5a3beb8a40e14b21aaa24973ac743d00
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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