Cesium carbonate → HCID 49758528, compound

HRID 445636Notes

Reaction equation

HRID 445636 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:9][C:10]1[NH:11][CH:12]=[CH:13][N:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 127492-MethylimidazoleHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 49758528HCID 49758528, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-bromo-2-chloro-pyridine (Aldrich, Buchs, Switzerland, 392 mg, 2.04 mmol), 2-methyl-1H-imidazole (Aldrich, Buchs, Switzerland, 251 mg, 3.06 mmol) and cesium carbonate (1.33 g, 4.08 mmol) in DMA (10 ml) was heated by microwave irradiation for 20 min at 100° C. and 2.5 h at 150° C. The reaction mixture was quenched with diluted brine (200 ml) and cooled. The precipitate was filtered, washed with water and dried to give the title compound as off-white solid. (HPLC: tR 2.03 min (Method A); M+H=238, 240 MS-ES).

Workup

  1. customThe reaction mixture was quenched with diluted brine (200 ml)
  2. temperaturecooled
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c0fbe965a5104fac996474fdedbe0194
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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