Reaction #595376

ord-8294b3517441414c81b59b42493ccab1

Reaction equation

Brc1n[nH]c2ccccc12
3-bromo-1H-indazole
CCN(CC)CC
triethylamine
N#Cc1ccccc1S(=O)(=O)Cl
2-cyanobenzene-1-sulfonyl chloride
N#Cc1ccccc1S(=O)(=O)n1nc(Br)c2ccccc21
3-bromo-1-(2-cyanophenylsulfonyl)-1H-indazole
Yield 97.4%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationAfter completion the reaction mixture was concentrated under reduced pressure
  2. 2
    Otherthe product was purified on SiO2 using 0% to 50% ethyl acetate in heptane as the eluent

Procedure

To a solution of 3-bromo-1H-indazole (200 mg, 1.02 mmol) in 2 ml CH2Cl2 was added triethylamine (308 mg, 3.05 mmol) and 2-cyanobenzene-1-sulfonyl chloride (205 mg, 1.02 mmol). The reaction mixture was stirred overnight at room temperature. After completion the reaction mixture was concentrated under reduced pressure and the product was purified on SiO2 using 0% to 50% ethyl acetate in heptane as the eluent to give 3-bromo-1-(2-cyanophenylsulfonyl)-1H-indazole (360 mg) as a yellow solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09095583B2uspto-grants-2015_08