Triethylamine → HCID 70098857, compound

HRID 467720Notes

Reaction equation

HRID 467720 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7](Br)[N:6]=1)=[O:4].[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C(N(CC)CC)C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2]>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([C:14]2[O:13][CH:17]=[CH:16][CH:15]=2)[N:6]=1)=[O:4]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateHCID 2734357Furan-2-boronic acid

Product 1

HCID 70098857HCID 70098857, compoundYield 60.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 152416121,1`-Bis(diphenylphosphino)ferroceneCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of Pd(OAc)2 (146 mg, 0.7 mmol) and 1,1-bis(diphenylphosphino)ferrocene (478 mg, 0.9 mmol) in DMF (65 ml) under an argon atmosphere was stirred at 50° for 15 min and cooled to rt. The reaction mixture was evacuated, then flushed with argon. 3-Amino-6-bromopyrazine-2-carboxylic acid methyl ester (5.0 g, 21.5 mmol), 2-furanboronic acid (2.65 g, 23.7 mmol) and triethylamine (4.3 ml) were added. The reaction mixture was again evacuated, then flushed with argon. The mixture was heated at 90° overnight. After cooling to rt, the black mixture was concentrated to dryness. The residue was dissolved in dichloromethane (800 ml), washed with water, dried over MgSO4, filtered and evaporated. The crude product was purified by silica gel chromatography using a n-heptane/EtOAc gradient for elution, providing the title compound as yellow solid (2.84 g, 60%).

Workup

  1. customThe reaction mixture was evacuated
  2. customflushed with argon
  3. customThe reaction mixture was again evacuated
  4. customflushed with argon
  5. temperatureThe mixture was heated at 90° overnight
  6. temperatureAfter cooling to rt
  7. concentrationthe black mixture was concentrated to dryness
  8. dissolutionThe residue was dissolved in dichloromethane (800 ml)
  9. washwashed with water
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customevaporated
  13. customThe crude product was purified by silica gel chromatography
  14. washfor elution

Sources & evidence

ORD record
ord-46b63bfe42534f978af35b45cb6d206a
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

Loading…