Ethanesulfonamide → N-((5-bromopyridin-3-yl)(cyclopentyl)methyl)ethanesulfonamide

HRID 1897782노트

반응식

HRID 1897782 반응식
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=O.[CH2:10]([S:12]([NH2:15])(=[O:14])=[O:13])[CH3:11].[CH:16]1([Mg]Br)[CH2:20][CH2:19][CH2:18][CH2:17]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:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[NH:15][S:12]([CH2:10][CH3:11])(=[O:14])=[O:13])[CH:5]=[N:4][CH:3]=1

참가 물질

6

반응물 3

HCID 73702EthanesulfonamideHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 178419650HCID 178419650, 화합물

생성물 1

HCID 59578440N-((5-bromopyridin-3-yl)(cyclopentyl)methyl)ethanesulfonamide수율 27.6%

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 1140Toluene용매

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온도
-40 °C

실험 절차

A mixture of 5-bromonicotinaldehyde (930 mg, 5 mmol), ethanesulfonamide (546 mg, 5.00 mmol) and titanium(IV) isopropoxide (2930 μl, 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 cyclopentylmagnesium bromide (2M in THF, 6.25 mL, 12.5 mmol) was added dropwise and the resulting mixture was slowly warmed up to 0° C. over 4 h. The reaction was quenched with a saturated NH4Cl solution. The mixture was filtered, separated, and extracted with CH2Cl2. The organic phase was dried over Na2SO4, filtered and concentrated, and the residue was purified by flash column (ethyl acetate/heptane, v/v, 10%-30%) to give a yellow oil (480 mg). ESI-MS m/z: 348.9 [M+1]+; 1H NMR (400 MHz, CDCl3): δ 1.13-1.80 (m, 7H), 1.26 (t, J=7.4 Hz, 3H), 1.97-2.05 (m, 1H), 2.20-2.29 (m, 1H), 2.67-2.92 (m, 2H), 4.27 (t, J=8.8 Hz, 1H), 5.59 (brs, 1H), 7.87 (s, 1H), 8.56 (s, 1H), 8.68 (s, 1H).

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. customThe reaction was quenched with a saturated NH4Cl solution
  7. filtrationThe mixture was filtered
  8. customseparated
  9. extractionextracted with CH2Cl2
  10. dry with materialThe organic phase was dried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customthe residue was purified by flash column (ethyl acetate/heptane, v/v, 10%-30%)

출처 및 근거

ORD 기록
ord-d7e825ed9935430398831b25d3039397
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08519142B2

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