2-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol → HCID 10109530, compound

HRID 586301Notes

Reaction equation

HRID 586301 reaction equation
[F:1][C:2]1[C:3]([C:9]2[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=2)=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.Br[C:19]1[N:23]2[N:24]=[CH:25][C:26]([C:28]([OH:31])([CH3:30])[CH3:29])=[N:27][C:22]2=[N:21][CH:20]=1>Cl>[F:1][C:2]1[C:3]([C:9]2[CH:10]=[C:11]([C:19]3[N:23]4[N:24]=[CH:25][C:26]([C:28]([OH:31])([CH3:29])[CH3:30])=[N:27][C:22]4=[N:21][CH:20]=3)[CH:12]=[CH:13][CH:14]=2)=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 22329528HCID 22329528, compound

Product 1

HCID 10109530HCID 10109530, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

3-(3,5-Difluoropyridin-2-yl)phenylboronic acid (25 mg, 0.11 mmol) was coupled to 2-(7-bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol (27 mg, 0.11 mmol) using the method of Example 20. Purification by chromatography (silica gel, 3% MeOH/CH2Cl2) gave impure product as a yellow solid. The product was then dissolved in hydrochloric acid (2 N, 50 ml), filtered and washed with diethyl ether (2×20 ml). The acid solution was cooled to 0° C. and neutralised with saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate (3×20 ml). The combined organic phases were dried over anhydrous magnesium sulphate, filtered and evaporated to give the title compound as a yellow solid: 1H. NMR (400 MHz, CDCl3) δ 1.72 (6H, s), 3.35 (1H, s), 7.32-7.38 (1H, m), 7.64 (1H, t, J 8 Hz), 7.95-7.98 (1H, m), 8.10-8.13 (1H, m), 8.33 (1H, 8), 8.48 (1H, d, J 3 Hz), 8.60-8.61 (1H, m), 8.79 (1H, s); MS (ES+) m/z 368 [M+H]+.

Workup

  1. customPurification by chromatography (silica gel, 3% MeOH/CH2Cl2)
  2. customgave impure product as a yellow solid
  3. filtrationfiltered
  4. washwashed with diethyl ether (2×20 ml)
  5. extractionextracted with ethyl acetate (3×20 ml)
  6. dry with materialThe combined organic phases were dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-549b4bce0d9242f3be0dc947632a6b27
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

Loading…