Pyridine → 6-Chloro-pyridine-3-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide

HRID 1049023Notes

Reaction equation

HRID 1049023 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:19][C:20]1[N:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[S:26]([C:23]2[CH:24]=[N:25][C:20]([Cl:19])=[CH:21][CH:22]=2)(=[O:28])=[O:27])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 185437114-Fluoro-N-(2-methylpropyl)aniline

Product 1

HCID 867218756-Chloro-pyridine-3-sulfonic acid (4-fluoro-phenyl)-isobutyl-amideYield 79.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-fluoro-phenyl)-isobutyl-amine (250 mg, 1.5 mmol) in DCM (5 mL) was added pyridine (242 μL, 3.0 mmol) followed by 6-chloropyridine-3-sulfonyl chloride (379 mg, 1.8 mmol) and the reaction was stirred at room temperature for 2 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 6-chloro-pyridine-3-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide (411 mg, 67%). LCMS (m/z, Method A) ES+ 343 [M+1]+.

Workup

  1. extractionextracted with DCM
  2. filtrationfiltered through a phase separator
  3. concentrationconcentrated
  4. customthen purified by silica gel column chromatography (0-20% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-8ae621d7c6074bd394fb42837b26a18e
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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