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

HRID 1890926ノート

反応式

HRID 1890926 の反応式
[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

参加物

5

反応物 3

HCID 1049PyridineHCID 24408BromineHCID 152903586-Quinolinyl trifluoromethanesulfonate

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-09c656a4ff984e74a261e348bd17b0a7
出典データセット
uspto-grants-2013_08
特許番号
US08507489B2

反応ノート

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