Dimethylformamide → Tert-butyl 4-(5-cyano-3-methylpyridin-2-yl)piperazine-1-carboxylate

HRID 1444119Notes

Reaction equation

HRID 1444119 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17](Br)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][N:23](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([C:22]#[N:23])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 46739269tert-Butyl 4-(5-bromo-3-methylpyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 66838837Tert-butyl 4-(5-cyano-3-methylpyridin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

Heat a solution of 4-(5-bromo-3-methyl-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (5.0 g, 14.0 mmol), Zn(CN)2 (989 mg, 8.4 mmol) and Pd(PPh3)4 (970 mg, 0.84 mmol), in dry DMF (50 mL) at 80° C. for 16 h under nitrogen in a sealed tube. Partition the reaction mixture between water and EtOAc. Wash the EtOAc layer with water (1×) and brine (1×), dry (Na2SO4) and concentrate under reduced pressure to give the title compound, and use immediately for the next reaction.

Workup

  1. customPartition the reaction mixture between water and EtOAc
  2. washWash the EtOAc layer with water (1×) and brine (1×)
  3. dry with materialdry (Na2SO4)
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-1c5d4e92ab6d43639bbd497abb5f5664
Source dataset
uspto-grants-2010_02
Patent number
US07662830B2

Reaction notes

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