5-Bromo-3-pyridinecarboxaldehyde → N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)propane-2-sulfonamide

HRID 391300

반응식

HRID 391300 반응식
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=O.[CH3:10][CH:11]([S:13]([NH2:16])(=[O:15])=[O:14])[CH3:12].[CH:17]1([Mg]Br)[CH2:19][CH2:18]1>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:9]=[C:6]([CH:7]([CH:17]2[CH2:19][CH2:18]2)[NH:16][S:13]([CH:11]([CH3:12])[CH3:10])(=[O:15])=[O:14])[CH:5]=[N:4][CH:3]=1

참가 물질

6

반응물 3

HCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 3549191Propane-2-sulfonamideHCID 178418630HCID 178418630, 화합물

생성물 1

HCID 59578391N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)propane-2-sulfonamide수율 66%

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 1140Toluene용매

반응 조건

온도
-40 °C

실험 절차

A mixture of 5-bromonicotinaldehyde (0.930 g, 5 mmol), propane-2-sulfonamide (0.616 g, 5.00 mmol) and titanium(IV) isopropoxide (2.93 mL, 10.00 mmol) in toluene (20 mL) was heated to reflux for 4 h. After concentration, the residue was dissolved in THF (25 mL) and cooled to −40° C. A solution of cyclopropylmagnesium bromide (25 mL, 12.50 mmol) was added dropwise and the resulting mixture was slowly warmed up to 0° C. over 4 h. After quenching with a NH4Cl solution, filtration and extraction with CH2Cl2, the organic phase was dried over Na2SO4, filtered and concentrated, to give a residue which was purified by flash column (ethyl acetate/heptane, v/v, 10%-35%) and to give a yellow solid (1.1 g). ESI-MS m/z: 335.0 [M+1]+.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. concentrationAfter concentration
  4. dissolutionthe residue was dissolved in THF (25 mL)
  5. temperaturethe resulting mixture was slowly warmed up to 0° C. over 4 h
  6. customAfter quenching with a NH4Cl solution, filtration and extraction with CH2Cl2
  7. dry with materialthe organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a residue which
  11. customwas purified by flash column (ethyl acetate/heptane, v/v, 10%-35%)

출처 및 근거

ORD 기록
ord-8e4e0f0205eb4c91aa016ffcf0ac200e
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383827B2

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