Cesium carbonate → HCID 66745402, compound

HRID 1959415Notes

Reaction equation

HRID 1959415 reaction equation
Br[C:2]1[N:3]=[C:4]([C:9]2[O:10][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:12][N:13]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[N:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1>CN(C=O)C.[Cu]>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([N:26]2[CH:31]=[CH:30][C:29](=[O:32])[CH:28]=[CH:27]2)=[N:3][C:4]=1[C:9]1[O:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:12][N:13]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 580843425-Bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amineHCID 178418642HCID 178418642, compound

Product 1

HCID 66745402HCID 66745402, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine (150.0 mg, 0.4715 mmol) in DMF (3.000 mL) was added copper (5.992 mg, 0.09430 mmol) and cesium carbonate (307.2 mg, 0.9430 mmol) followed by pyridin-4-ol (448.4 mg, 4.715 mmol) and the reaction mixture heated at 160° C. in the microwave for 1 h. The reaction mixture was filtered and washed with DMF (2 mL). Ethyl acetate and water were added to the filtrate and the layers separated. The aqueous layer was extracted further with ethyl acetate (3×5 mL) and the combined organic extracts were washed with water (3×5 mL). The organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The material was triturated with a mixture of methanol and ether to leave the product. (42.6 mg, 25% yield); 1H NMR (400 MHz, DMSO) d 6.33 (d, 2H), 7.69 (s, 2H), 8.15-8.18 (m, 2H), 8.35 (d, 2H) and 8.78 (s, 1H) ppm; MS (ES+) 333.11

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with DMF (2 mL)
  3. additionEthyl acetate and water were added to the filtrate
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted further with ethyl acetate (3×5 mL)
  6. washthe combined organic extracts were washed with water (3×5 mL)
  7. dry with materialThe organic extracts were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe material was triturated with a mixture of methanol and ether
  11. customto leave the product

Sources & evidence

ORD record
ord-e2ce0f849708446782a86ac32079bb56
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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