Potassium Carbonate → HCID 22607799, compound

HRID 2307766Notes

Reaction equation

HRID 2307766 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17](Br)[CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:12][C:13]1[CH:18]=[C:17]([O:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][N:6]=[CH:7]3)[CH:16]=[N:15][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 30386Isoquinolin-5-olHCID 693693,5-Dibromopyridine

Product 1

HCID 22607799HCID 22607799, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
240 °C

Procedure

A sealed tube was charged with 5-hydroxyisoquinoline (0.15 g, 1.03 mmol), 3,5-dibromopyridine (0.24 g, 1.03 mmol), potassium carbonate (0.27 g, 2.0 mmol) and DMF (4 mL). The reaction was heated to 240° C. for 10 minutes in a personal chemistry microwave. The reaction was partitioned between water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate. The combined extracts were concentrated and the residue was purified by flash column chromatography on silica gel with 2:1 ethyl acetate/hexanes to provide the desired product (0.071 g, 23%).

Workup

  1. customThe reaction was partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. concentrationThe combined extracts were concentrated
  4. customthe residue was purified by flash column chromatography on silica gel with 2:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4af185c7f9aa495b9fb69886035ca585
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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