Reaction #710545

Reaction equation

NaHCO3

(4-fluoro-phenyl)-isobutyl-amine

5-bromo-pyridine-2-sulfonyl chloride

pyridine

→

5-bromo-pyridine-2-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide

Yield 82.9%

Solvents

Water

DCM

DCM

Conditions

Workup

1. 1
   Extractionextracted with DCM
2. 2
   Filtrationfiltered through a phase separator
3. 3
   Concentrationconcentrated
4. 4
   Otherthen purified by silica gel column chromatography (0-20% EtOAc in cyclohexane)

Procedure

To a solution of 5-bromo-pyridine-2-sulfonyl chloride (330 mg, 1.29 mmol) in DCM (10 mL) was added pyridine (208 μL, 2.57 mmol) followed by a solution of (4-fluoro-phenyl)-isobutyl-amine (215 mg, 1.29 mmol) in DCM (10 mL) and the reaction was stirred at room temperature for 16 hours. Water and saturated aqueous NaHCO3 were added and then extracted with DCM, filtered through a phase separator, concentrated then purified by silica gel column chromatography (0-20% EtOAc in cyclohexane) to give 5-bromo-pyridine-2-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide (414 mg, 78%). LCMS (m/z, Method A) ES+ 387/389 [M+1]+.

Source