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

HRID 1370588노트

반응식

HRID 1370588 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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):

후처리

  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

출처 및 근거

ORD 기록
ord-ddeef1df2bc9424bbcff886ed4886177
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06583162B1

반응 노트

불러오는 중…