Pyridine → Trifluoromethanesulfonic acid 3-bromo-quinolin-6-yl ester

HRID 1890926노트

반응식

HRID 1890926 반응식
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[Br:25]Br>C(Cl)(Cl)(Cl)Cl>[Br:25][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][C:7]([O:11][S:12]([C:15]([F:18])([F:16])[F:17])(=[O:13])=[O:14])=[CH:8][CH:9]=2

참가 물질

5

반응물 3

HCID 1049PyridineHCID 24408BromineHCID 152903586-Quinolinyl trifluoromethanesulfonate

생성물 1

HCID 57911035Trifluoromethanesulfonic acid 3-bromo-quinolin-6-yl ester수율 26.1%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

To a mixture of trifluoromethanesulfonic acid quinolin-6-yl ester (3.88 g, 14 mmol) and pyridine (2.26 mL, 28 mmol) in CCl4 (50 mL) was added bromine (0.86 mL, 16.8 mmol) dropwise. The mixture was heated to reflux for 2 hrs and cooled to room temperature. The liquid in the flask was decanted and washed with NaHCO3 and water. The dark solid on the bottom of the flask was treated with NaHCO3 and dichloromethane. The combined organic layers were washed with water again and dried before being evaporated to dryness. The crude product was purified by flash column chromatography eluting with petroleum ether/ethyl acetate (10/1˜1/1) to give 1.3 g of trifluoromethanesulfonic acid 3-bromo-quinolin-6-yl ester: 1H NMR (300 MHz, CDCl3) δ: 7.62 (m, 1H), 7.68 (d, 1H), 8.20 (d, 1H), 8.36 (m, 1H), 8.98 (d, 1H); MS (m/z) 356 [M+H]+.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hrs
  3. customThe liquid in the flask was decanted
  4. washwashed with NaHCO3 and water
  5. additionThe dark solid on the bottom of the flask was treated with NaHCO3 and dichloromethane
  6. washThe combined organic layers were washed with water again
  7. customdried
  8. custombefore being evaporated to dryness
  9. customThe crude product was purified by flash column chromatography
  10. washeluting with petroleum ether/ethyl acetate (10/1˜1/1)

출처 및 근거

ORD 기록
ord-09c656a4ff984e74a261e348bd17b0a7
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507489B2

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