Water → 6-Bromo-8-(2-pyridin-4-yl-imidazol-1-yl)-imidazo[1,2-a]pyrazine

HRID 457671

Reaction equation

HRID 457671 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.[Br:14][C:15]1[N:16]=[C:17](Br)[C:18]2[N:19]([CH:21]=[CH:22][N:23]=2)[CH:20]=1.O>CN(C=O)C>[Br:14][C:15]1[N:16]=[C:17]([N:3]2[CH:7]=[CH:6][N:5]=[C:4]2[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[C:18]2[N:19]([CH:21]=[CH:22][N:23]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3168174-(1H-Imidazol-2-yl)-pyridineHCID 150258436,8-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 184403196-Bromo-8-(2-pyridin-4-yl-imidazol-1-yl)-imidazo[1,2-a]pyrazineYield 43.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (NaH) (730 milligrams (mg) of a 95% dispersion in mineral oil) is added to a solution of 4-(1H-Imidazol-2-yl)-pyridine (4.0 g) in N,N,-dimethylformamide (DMF) (150 ml) and the mixture is stirred at room temperature (rt) for 0.5 hr. A solution of 6,8-dibromoimidazo[1,2-a]pyrazine (3) (7.63 g) in DMF (10 ml) is added. The mixture is stirred at room temperature (rt) for 16 hr. Water (50 ml) is added and the mixture is extracted with ethyl acetate (3×70 ml); extracts are washed with water (2×50 ml) and brine (1×50 ml), dried over sodium sulfate (Na2SO4), and evaporated in vacuo. Purification on SiO2 (5% MeOH, DCM) yielded 6-Bromo-8-(2-pyridin-4-yl-imidazol-1-yl)-imidazo[1,2-a]pyrazine (4) (4.08 g) as an off-white solid.

Workup

  1. stirringThe mixture is stirred at room temperature (rt) for 16 hr
  2. extractionthe mixture is extracted with ethyl acetate (3×70 ml)
  3. washextracts are washed with water (2×50 ml) and brine (1×50 ml)
  4. dry with materialdried over sodium sulfate (Na2SO4)
  5. customevaporated in vacuo
  6. customPurification on SiO2 (5% MeOH, DCM)

Sources & evidence

ORD record
ord-3db6365ebb5744728b09dcefa8587a72
Source dataset
uspto-grants-2007_03
Patent number
US07189723B2

Linked notes

Loading…