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

HRID 1372927

Reaction equation

HRID 1372927 reaction equation
[H-].[Na+].[C:3]1([CH3:14])[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][NH:12][CH:13]=2)=[CH:5][CH:4]=1.[Br:15][C:16]1[N:17]=[C:18](Br)[C:19]2[N:20]([CH:22]=[CH:23][N:24]=2)[CH:21]=1.O>CN(C=O)C.C(OCC)C>[Br:15][C:16]1[N:17]=[C:18]([N:12]2[CH:13]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH3:14])=[CH:8][CH:7]=3)[N:10]=[CH:11]2)[C:19]2[N:20]([CH:22]=[CH:23][N:24]=2)[CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 150258436,8-Dibromoimidazo[1,2-a]pyrazineHCID 178423883HCID 178423883, compound

Product 1

HCID 210728866-Bromo-8-(4-p-tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazineYield 84.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (NaH) (144 milligrams (mg) of a 60% dispersion in mineral oil) is added to a solution of 4-p-tolyl-1H-imidazole (571 mg) in N,N,-dimethylformamide (DMF) (10 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) (1.0 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 magnesium sulfate (MgSO4), and evaporated in vacuo to give a waxy solid. The solid is slurried with a little diethyl ether and filtered to give 6-Bromo-8-(4-p-tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazine (4) (1.08 g) as a light brown 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 magnesium sulfate (MgSO4)
  5. customevaporated in vacuo
  6. customto give a waxy solid
  7. filtrationfiltered

Sources & evidence

ORD record
ord-dfd4e2d547584077899f362d469a5d8e
Source dataset
uspto-grants-2007_01
Patent number
US07160885B2

Linked notes

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