Dimethylformamide → HCID 53946632, compound

HRID 1459633Notes

Reaction equation

HRID 1459633 reaction equation
CN(C=O)C.I[C:7]1[C:12]([CH3:13])=[N:11][CH:10]=[CH:9][N:8]=1.[CH:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)=[O:15].CCN(CC)CC>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(Cl)(Cl)Cl>[CH3:13][C:12]1[C:7]([C:19]2[CH:20]=[CH:21][C:16]([CH:14]=[O:15])=[CH:17][CH:18]=2)=[N:8][CH:9]=[CH:10][N:11]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 5910734-Formylphenylboronic AcidHCID 108786642-IODO-3-METHYLPYRAZINE

Product 1

HCID 53946632HCID 53946632, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

To a 100 ml round bottomed flask with stirring bar and an argon inlet was added Pd(OAc)2 (0.036 g, 0.15 mmol), bisdiphenylphosphinoferrocene (DPPF, 0.12 g, 0.2 mmol), and 15 ml of DMF were heated to 50° for 15 minutes. Cooled the reaction to room temperature then added 2-iodo-3-methyl-pyrazine (1.2 g, 5.4 mmol)(5). (a prep from Albert Hirschberg et al. J.Org. Chem. Jun.,1961 p1907-1912) and 4-formylbenzenboronic acid (0.90 g, 6.0 mmol) and Et3N (1.05 ml, 7.5 mmol). The mixture was heated to 90° C. for 10 h. Removed solvent in vacuo, taken up with CHCl3 and washed with diluted NH4OH. The organic layer was dried (MgSO4), filtered and concentrated to yield a black oil. This material was chromatographed (silica gel, 30% EtOAc/Hexane) to afford the title product.

Workup

  1. temperaturewere heated to 50° for 15 minutes
  2. temperatureCooled
  3. customthe reaction to room temperature
  4. washwashed with diluted NH4OH
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a black oil
  9. customThis material was chromatographed (silica gel, 30% EtOAc/Hexane)

Sources & evidence

ORD record
ord-ae9eb7c78185463e975496bacac934ba
Source dataset
uspto-grants-1998_12
Patent number
US05854264

Reaction notes

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