Sodium Cyanide → 6-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile

HRID 1037560Notes

Reaction equation

HRID 1037560 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2Cl.[C-:19]#[N:20].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2[C:19]#[N:20]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 677760136-bromo-3-chloro-2-(4-fluorophenyl)-2H-indazole

Product 1

HCID 675136096-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrileYield 54.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a stirred solution of compound (xiii) (4.49 g, 12.86 mmol) in DMF (50 mL) was added sodium cyanide (1.34 g, 27.73 mmol) at RT and the reaction mixture was then heated at 130° C. for 2 h. The reaction mixture was then diluted with saturated FeCl3 solution and extracted with EtOAc (3×75 mL). The combined organic layers were washed with water, dried (Na2SO4) and concentrated to give the crude product which was purified by column chromatography on 100-200 mesh silica gel eluting with EtOAc/hexane (2-4%) to give 6-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile (xiv) (2.2 g, 50%) as white solid. ESI-MS m/z calculated for [M+H]+: 317.99; found: 317.90.

Workup

  1. extractionextracted with EtOAc (3×75 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas purified by column chromatography on 100-200 mesh silica gel eluting with EtOAc/hexane (2-4%)

Sources & evidence

ORD record
ord-523d92fec85e47b1901a491436473d00
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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