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

HRID 418990

Reaction equation

[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

Participants

Conditions

Temperature: 60 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-bdf7097ebde54bb28fa3f5be240f6d06
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093247B2

Linked notes

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