Dimethylformamide → HCID 54057074, compound

HRID 1585897Notes

Reaction equation

HRID 1585897 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-4a570c90dec54eec8019776bc53ab3fe
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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