Ethanesulfonamide → N-(2-(5-bromopyridin-3-yl)propan-2-yl)ethanesulfonamide

HRID 391306Notes

Reaction equation

HRID 391306 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH3:9])[CH:5]=[N:6][CH:7]=1.[CH2:11]([S:13]([NH2:16])(=[O:15])=[O:14])[CH3:12].[CH3:17][Mg]Br>C1(C)C=CC=CC=1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:16][S:13]([CH2:11][CH3:12])(=[O:15])=[O:14])([CH3:9])[CH3:17])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 73702EthanesulfonamideHCID 8204233-Acetyl-5-bromopyridineHCID 178418573HCID 178418573, compound

Product 1

HCID 59578400N-(2-(5-bromopyridin-3-yl)propan-2-yl)ethanesulfonamideYield 11.4%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1-(5-bromo-pyridin-3-yl)-ethanone (200 mg, 1.000 mmol), ethanesulfonamide (136 mg, 1.250 mmol) and titanium(IV) isopropoxide (586 μL, 2.0 mmol) in toluene (20 mL) was heated to reflux for 8 h. After concentration, the residue was dissolved in THF (5 mL). A solution of methylmagnesium bromide (1000 μl, 3.00 mmol) was added dropwise at −50° C. The resulting mixture was slowly warmed up to room temperature over a course of 2 h. The mixture was stirred at this temperature overnight and quenched with NH4Cl solution. After filtration, wash with CH2Cl2 and concentration, the residue was purified by flash column (Ethyl acetate/heptane, v/v, 10% to 50%) and yielded a yellow oil (35 mg). ESI-MS m/z: 309.1 [M+1]+, Retention time=1.22 min. 1H NMR (400 MHz, CDCl3): δ 1.43 (t, J=7.4 Hz, 3H), 1.84 (s, 6H), 2.98 (q, J=7.4 Hz, 2H), 5.07 (brs, 1H), 8.04 (s, 1H), 8.66 (s, 1H), 8.77 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8 h
  3. concentrationAfter concentration
  4. dissolutionthe residue was dissolved in THF (5 mL)
  5. customquenched with NH4Cl solution
  6. filtrationAfter filtration
  7. washwash with CH2Cl2 and concentration
  8. customthe residue was purified by flash column (Ethyl acetate/heptane, v/v, 10% to 50%)

Sources & evidence

ORD record
ord-3e35682ea64b41a9b4eeb9c4d572b9cc
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

Loading…