Pyridine → N-(3-bromo-2,4-difluorophenyl)propane-1-sulfonamide

HRID 629501Notes

Reaction equation

HRID 629501 reaction equation
[Br:1][C:2]1[C:3]([F:10])=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[CH2:11]([S:14](Cl)(=[O:16])=[O:15])[CH2:12][CH3:13].N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:1][C:2]1[C:3]([F:10])=[C:4]([NH:5][S:14]([CH2:11][CH2:12][CH3:13])(=[O:16])=[O:15])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

7

Reactant 4

HCID 1049PyridineHCID 662791-Propanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 137327463-Bromo-2,4-difluoroaniline

Product 1

HCID 51034457N-(3-bromo-2,4-difluorophenyl)propane-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-2,4-difluoroaniline (4.16 g, 20 mmol, EP184384), n-propanesulfonyl chloride (4.6 ml, 40 mmol), pyridine (8 ml), DMAP (97 mg), and DCM (100 ml) was stirred at rt for 16 h. Aqueous sodium bicarbonate solution was added and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium bicarbonate and brine. The crude product was purified by silica gel chromatography (8:1 to 3:1 hexanes/ethyl acetate eluant) to give the title compound. MS m/z 313.9 (M+1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with aqueous sodium bicarbonate and brine
  3. customThe crude product was purified by silica gel chromatography (8:1 to 3:1 hexanes/ethyl acetate eluant)

Sources & evidence

ORD record
ord-dd51e7cd9444496188d41a69f903deaa
Source dataset
uspto-grants-2016_04
Patent number
US09314464B2

Reaction notes

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