Pyridine → HCID 69812329, compound

HRID 535733Notes

Reaction equation

HRID 535733 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH2:5].[CH:10]([S:13](Cl)(=[O:15])=[O:14])([CH3:12])[CH3:11].N1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][S:13]([CH:10]([CH3:12])[CH3:11])(=[O:15])=[O:14])[CH:6]=[C:7]([CH3:9])[CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 824082-Propanesulfonyl chlorideHCID 30185263-Bromo-5-methylaniline

Product 1

HCID 69812329HCID 69812329, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-5-methylaniline (500 mg, 2.2 mmol) in DCM (5 mL), isopropylsulfonylchloride (0.3 mL, 2.7 mmol) was added, followed by the addition of pyridine (0.45 mL, 5.6 mmol). The reaction was stirred at room temperature for 25 hours at which time it was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4), and absorbed onto silica. Purification by flash chromatography (SiO2, 0-30% EtOAc in hexanes) afforded N-(3-bromo-5-methylphenyl)propane-2-sulfonamide (558 mg, 1.9 mmol, 85%) as a peach colored solid: 1H NMR (400 MHz, CDCl3) δ 1.41 (d, J=6.7 Hz, 6H) 2.31 (s, 3H) 3.33 (m, 1H) 6.84 (br s, 1H) 6.97 (s, 1H) 7.10 (s, 1H) 7.21 (s, 1H).

Workup

  1. customwas quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customabsorbed onto silica
  6. customPurification by flash chromatography (SiO2, 0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d673891a404c4c28b2f830fee1c6de4c
Source dataset
uspto-grants-2014_10
Patent number
US08859548B2

Reaction notes

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