Cesium carbonate → 5-(4-Methyl-1H-imidazol-1-yl)pyridin-2-amine

HRID 1036219Notes

Reaction equation

HRID 1036219 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:9][C:10]1[N:11]=[CH:12][NH:13][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I.CN(C=O)C>[CH3:9][C:10]1[N:11]=[CH:12][N:13]([C:2]2[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=2)[CH:14]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 885792-Pyridinamine, 5-iodo-HCID 178418800HCID 178418800, compound

Product 1

HCID 575128615-(4-Methyl-1H-imidazol-1-yl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

To a seal tube charged with 5-iodopyridin-2-amine 143-1 (1.1 g, 5 mmol), 4-methyl-1H-imidazole 143-2 (0.61 g, 7.4 mmol), CuI (0.31 g, 1.63 mmol) and Cs2CO3 (3.25 g, 10 mmol) was added DMF (10 mL). The reaction vessel was flushed with nitrogen and sealed. The reaction was stirred at room temperature for 30 minutes before being heated up to 110° C. for 24 hours. The reaction was diluted into ethyl acetate and the salt was removed by filtration. The filtrate was dried and the residue was purified by silica gel flash chromatography, eluted with 10% methanol in ethyl acetate to give 5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine 143-3 as off-white solid. MS m/z 175.2 (M+1).

Workup

  1. customThe reaction vessel was flushed with nitrogen
  2. customsealed
  3. temperaturebefore being heated up to 110° C. for 24 hours
  4. additionThe reaction was diluted into ethyl acetate
  5. customthe salt was removed by filtration
  6. customThe filtrate was dried
  7. customthe residue was purified by silica gel flash chromatography
  8. washeluted with 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-4b96c06c17fe4ca982ae692719079982
Source dataset
uspto-grants-2013_10
Patent number
US08546396B2

Reaction notes

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