Triethylamine → 3-bromo-1-(2-cyanophenylsulfonyl)-1H-indazole

HRID 508194Notes

Reaction equation

HRID 508194 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.C(N(CC)CC)C.[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26](Cl)(=[O:28])=[O:27])#[N:19]>C(Cl)Cl>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:26]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[C:18]#[N:19])(=[O:28])=[O:27])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5223472-Cyanobenzenesulfonyl ChlorideHCID 178419483HCID 178419483, compound

Product 1

HCID 1182647323-bromo-1-(2-cyanophenylsulfonyl)-1H-indazoleYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

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

Sources & evidence

ORD record
ord-8294b3517441414c81b59b42493ccab1
Source dataset
uspto-grants-2015_08
Patent number
US09095583B2

Reaction notes

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