2-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol → HCID 9968258, compound

HRID 586298Notes

Reaction equation

HRID 586298 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]=[N:13][CH: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]=[N:13][CH:12]=1

Participants

3

Reactant 2

HCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 22329487HCID 22329487, compound

Product 1

HCID 9968258HCID 9968258, compound

Procedure

4-Fluoro-3-(pyridazin-4-yl)phenylboronic acid (300 mg, 1.38 mmol) was coupled to 2-(7-bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol (100 mg, 0.39 mmol) using the method of Example 20. Purification by chromatography (silica gel, 3% MeOH/CH2Cl2) then dissolving in toluene and washing with water followed by recrystallisation from hot toluene with isohexane gave the title compound as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 1.73 (6H, s), 3.23 (1H, s), 7.41 (1H, dd, J 10, 9 Hz), 7.75-7.78 (1H, m), 8.08-8.13 (1H, m), 8.28 (1H, s), 8.31 (1H, dd, J 7, 2 Hz), 8.83 (1H, s), 9.32 (1H, dd, J 5, 1 Hz), 9.50-9.52 (1H, m); MS (ES+) m/z 351 [M+H]+.

Workup

  1. customPurification by chromatography (silica gel, 3% MeOH/CH2Cl2)
  2. dissolutionthen dissolving in toluene
  3. washwashing with water
  4. customfollowed by recrystallisation from hot toluene with isohexane

Sources & evidence

ORD record
ord-f47f86822a504d1388c0648c75782a3c
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

Loading…