Triethylamine → (E)-2-(2-Amino-5-chloro-3-pyridinyl)-N-methyl-1-ethenesulphonamide

HRID 1838075Notes

Reaction equation

HRID 1838075 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:10][NH:11][S:12]([CH:15]=[CH2:16])(=[O:14])=[O:13].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:9][C:3]1[C:2](/[CH:16]=[CH:15]/[S:12]([NH:11][CH3:10])(=[O:14])=[O:13])=[CH:7][C:6]([Cl:8])=[CH:5][N:4]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 27639713-Bromo-5-chloropyridin-2-amineHCID 21895383N-Methylethenesulfonamide

Product 1

HCID 18752899(E)-2-(2-Amino-5-chloro-3-pyridinyl)-N-methyl-1-ethenesulphonamideYield 25%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromo-5-chloro-2-pyridinamine (414 mg, 2 mmol), N-methyl ethene sulphonamide (266 mg, 2.2 mmol) and triethylamine (555 μl, 4 mmol), palladium acetate (18 mg, 0.08 mmol) and tri-o-tolylphosphine (50 mg, 0.16 mmol) in DMF (0.5 ml) in a Teflon™ pressure vessel was microwaved for 30 sec (full power), allowed to cool to RT and irradiated for a further 30 sec. After allowing to cool, the reaction mixture was diluted with water, extracted with EtOAc and the organic phase washed with saturated brine, dried over MgSO4, and concentrated to a brown semi-solid. Purification by column chromatography on silica gel eluting with methylene chloride—methanol (95:5), and then crystallisation from methanol gave the title compound (130 mg, 0.5 mmol):

Workup

  1. customwas microwaved for 30 sec (full power)
  2. customirradiated for a further 30 sec
  3. temperatureto cool
  4. extractionextracted with EtOAc
  5. washthe organic phase washed with saturated brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to a brown semi-solid
  8. customPurification by column chromatography on silica gel eluting with methylene chloride—methanol (95:5)
  9. customcrystallisation from methanol

Sources & evidence

ORD record
ord-38510d8b95f54db9a1fe12e1253e83cd
Source dataset
uspto-grants-2004_01
Patent number
US06673789B2

Reaction notes

Loading…