Pyrrolidine → 4-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine

HRID 1603562Notes

Reaction equation

HRID 1603562 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[C:4]([Br:18])[N:3]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>O1CCOCC1>[Br:18][C:4]1[CH:5]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:7]=[C:2]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[N:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 110146744-(2,6-dibromopyridin-4-yl)sulfonylaniline

Product 1

HCID 69186894-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamineYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.0 g (0.00255 mol) of 4-(2,6-dibromopyridine-4-sulphonyl)-phenylamine was dissolved in 25 ml of dioxane and treated with 2.1 ml of pyrrolidine. The mixture was stirred at room temperature for 4 hrs., the solvent was removed and the residue was chromatographed on silica gel with ethyl acetate/hexane 1:1. There was obtained 0.9 g (93%) of 4-(2-bromo-6-pyrrolidin-1-yl-pyridine-4-sulphonyl)- phenylamine as beige crystals; m.p.: 216° C. (dec).

Workup

  1. custom, the solvent was removed
  2. customthe residue was chromatographed on silica gel with ethyl acetate/hexane 1:1

Sources & evidence

ORD record
ord-e1edbf4c6cce451ea2cae81604a6576d
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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