3-Amino-2-bromo-5-chloropyridine → N-(2-Bromo-5-chloro-pyridin-3-yl)-4-chloro-3-trifluoromethyl-benzenesulfonamide

HRID 418990

Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].[Br:16][C:17]1[C:22]([NH2:23])=[CH:21][C:20]([Cl:24])=[CH:19][N:18]=1>N1C=CC=CC=1>[Br:16][C:17]1[C:22]([NH:23][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:12]([F:15])([F:14])[F:13])[CH:4]=2)(=[O:10])=[O:9])=[CH:21][C:20]([Cl:24])=[CH:19][N:18]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A mixture of 4-chloro-3-trifluoromethyl-benzenesulfonyl chloride (1.5 g, 5.3 mmol) and 2-bromo-5-chloro-pyridin-3-ylamine (500 mg, 2.4 mmol) dissolved in pyridine (20 mL) was heated at 60° C. for 16 h. The solvent was evaporated and the residue suspended in a 1:1 mixture of 2 M NaOH and methanol (20 mL) and heated at 70° C. for 30 min. The methanol was evaporated under reduced pressure and the residue diluted with 15 mL water. The solution was cooled on ice bath and the pH was adjusted to 3 by drop wise addition of concentrated HCl. The solid formed was collected by filtration and the product was purified by flash chromatography on silica gel column to afford the desired product. MS m/z: 450.8 (M+H).

Aufarbeitung

customThe solvent was evaporated
additionthe residue suspended in a 1:1 mixture of 2 M NaOH and methanol (20 mL)
temperatureheated at 70° C. for 30 min
customThe methanol was evaporated under reduced pressure
additionthe residue diluted with 15 mL water
temperatureThe solution was cooled on ice bath
additionthe pH was adjusted to 3 by drop wise addition of concentrated HCl
customThe solid formed
filtrationwas collected by filtration
customthe product was purified by flash chromatography on silica gel column

Quellen und Nachweise

ORD-Eintrag: ord-bdf7097ebde54bb28fa3f5be240f6d06
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08093247B2

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