Dimethylformamide → HCID 86694708, compound

HRID 475149Notes

Reaction equation

HRID 475149 reaction equation
Br[C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[CH3:12][N:13](C=O)C>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-]#N.[C-]#N.[Zn+2]>[Cl:11][C:9]1[CH:10]=[C:2]([C:12]#[N:13])[C:3]2[CH:4]=[N:5][NH:6][C:7]=2[CH:8]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 247281004-Bromo-6-chloro-1H-indazole

Product 1

HCID 86694708HCID 86694708, compoundYield 86.9%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

A mixture of 4-bromo-6-chloro-1H-indazole (3.0 g, 12.9 mmol), Pd(PPh3)4 (2.24 g, 1.94 mmol), and Zn(CN)2 (9.22 g, 25.8 mmol) in DMF (50 mL) under nitrogen was heated at 120° C. for 16 h. The reaction mixture was quenched with water and extracted with EtOAc (50 mL×5). The combined extracts were washed with brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to afford 6-chloro-1H-indazole-4-carbonitrile as white solid (2.0 g, 86.9%).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc (50 mL×5)
  3. washThe combined extracts were washed with brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c60004d42aa1406cbbb45e4ca3812d44
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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