Dimethylformamide → HCID 54057074, compound

HRID 1421717Notes

Reaction equation

HRID 1421717 reaction equation
C(OC([N:8]1[C:16]2[CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]([C:24]3[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=3)[C:11]=2[N:10]=[CH:9]1)=O)(C)(C)C.[CH3:31][N:32](C=O)C>[C-]#N.[C-]#N.[Zn+2]>[C:20]([O:19][C:17]([N:13]1[CH2:14][CH2:15][C:16]2[NH:8][CH:9]=[N:10][C:11]=2[CH:12]1[C:24]1[CH:25]=[CH:26][C:27]([C:31]#[N:32])=[CH:28][CH:29]=1)=[O:18])([CH3:21])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 537517454-(4-Bromo-phenyl)-6,7-dihydro-4H-imidazo[4,5-c]pyridine-1,5-dicarboxylic acid di-tert-butyl ester

Product 1

HCID 54057074HCID 54057074, compound

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
80 °C

Procedure

4-(4-Bromo-phenyl)-6,7-dihydro-4H-imidazo[4,5-c]pyridine-1,5-dicarboxylic acid di-tert-butyl ester (0.55 g, 1.14 mmol) and Zn(CN)2 (0.13 g, 1.14 mmol) were stirred in anh. DMF (10 mL) and degassed with Ar for 15 min. Tetrakis(triphenylphosphine)-palladium(0) was added to the solution and stirred at 80° C. under Ar overnight. The solution was concentrated in vacuo, partitioned between EtOAc and sat. NaHCO3 soln, washed with H2O, brine, and dried over MgSO4. Filtration, concentration, and silica gel chromatography (0-2% MeOH/CH2Cl2 with NH4OH) gave the title compound.

Workup

  1. customdegassed with Ar for 15 min
  2. additionTetrakis(triphenylphosphine)-palladium(0) was added to the solution
  3. concentrationThe solution was concentrated in vacuo
  4. custompartitioned between EtOAc and sat. NaHCO3 soln
  5. washwashed with H2O, brine
  6. dry with materialdried over MgSO4
  7. filtrationFiltration, concentration, and silica gel chromatography (0-2% MeOH/CH2Cl2 with NH4OH)

Sources & evidence

ORD record
ord-25bb5b87a368467b9b253d46c530ae95
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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