Potassium Carbonate → Thiophen-2-yl-imidazo[1,2-a]pyrazin-8-ylamine

HRID 457021Notes

Reaction equation

HRID 457021 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH:11][CH3:12])[C:5]2=[N:4][CH:3]=1.[S:13]1C=[CH:16][CH:15]=[C:14]1B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCCC1.O>[S:13]1[CH:14]=[CH:15][CH:16]=[C:12]1[NH:11][C:10]1[C:5]2[N:6]([CH:2]=[CH:3][N:4]=2)[CH:7]=[CH:8][N:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339602-Thiopheneboronic acidHCID 3088360Imidazo(1,2-a)pyrazin-8-amine, 3-bromo-N-methyl-

Product 1

HCID 11148632Thiophen-2-yl-imidazo[1,2-a]pyrazin-8-ylamineYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (3-bromo-imidazo[1,2-a]pyrazin-8-yl)-methyl-amine (50 mg, 0.2 mmol) in tetrahydrofuran (2 ml) under nitrogen was added 2-thiopheneboronic acid (41 mg, 0.3 mmol), K2CO3 (1.1 ml of a 1 M solution in water) and 16 mg (0.1 mmol) of PdCl2(Dppf)CH2Cl2 (16 mg, 0.1 eq). The mixture was heated at 70° C. in a sealed tube overnight. The product was precipitated by adding methanol. The filtrate was evaporated and purified by preparative thin layer chromatography on silica gel to give additional title compound for a total of 45 mg (100% yield).

Workup

  1. customThe product was precipitated
  2. additionby adding methanol
  3. customThe filtrate was evaporated
  4. custompurified by preparative thin layer chromatography on silica gel

Sources & evidence

ORD record
ord-ef2eb0baa86b4144b9be2837f4728db2
Source dataset
uspto-grants-2007_03
Patent number
US07186832B2

Reaction notes

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