Triethylamine → 3-bromo-1-(2-(trifluoromethyl)phenylsulfonyl)-1H-indazole

HRID 508193Notes

Reaction equation

HRID 508193 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.[F:18][C:19]([F:31])([F:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26](Cl)(=[O:28])=[O:27]>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:19]([F:18])([F:30])[F:31])(=[O:28])=[O:27])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 178419483HCID 178419483, compound

Product 1

HCID 681592723-bromo-1-(2-(trifluoromethyl)phenylsulfonyl)-1H-indazoleYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-bromoindazole (500 mg, 2.54 mmol) in 8 ml CH2Cl2 was added triethyl amine (1.06 ml, 7.61 mmol) at room temperature. To this yellow solution was added 2-(trifluoromethyl)benzenesulfonyl chloride (0.392 ml, 2.54 mmol) and the reaction mixture was stirred for 3 h at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was purified on SiO2 using 5% to 20% ethyl acetate in heptane to give 3-bromo-1-(2-(trifluoromethyl)phenylsulfonyl)-1H-indazole (894 mg)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified on SiO2 using 5% to 20% ethyl acetate in heptane

Sources & evidence

ORD record
ord-9bb6984f92b749809f85999c622bd14c
Source dataset
uspto-grants-2015_08
Patent number
US09095583B2

Reaction notes

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