4-Bromophenol → trans-N-[4-(4-bromophenoxy)tetrahydrofuran-3-yl]propane-2-sulfonamide

HRID 2360319노트

반응식

HRID 2360319 반응식
CS([O:5][C@H:6]1[C@H:10]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:9][O:8][CH2:7]1)(=O)=O.[Br:18][C:19]1[CH:24]=[CH:23][C:22](O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)(O)[O-].[Na+]>C(#N)C>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([O:5][C@@H:6]2[CH2:7][O:8][CH2:9][C@H:10]2[NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 78084-BromophenolHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 86653047HCID 86653047, 화합물

생성물 1

HCID 67194484trans-N-[4-(4-bromophenoxy)tetrahydrofuran-3-yl]propane-2-sulfonamide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

In a microwave vial, a solution of trans-4-[(isopropylsulfonyl)amino]tetrahydrofuran-3-yl methanesulfonate (546 mg, 1.90 mmol) in acetonitrile (8 mL) was combined with 4-bromophenol (97%, 407 mg, 2.28 mmol) and cesium carbonate (929 mg, 2.85 mmol). The reaction was irradiated in a microwave reactor at 160° C. for 2 hours, then cooled to room temperature and treated with saturated aqueous sodium bicarbonate solution (10 mL). The reaction was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (Gradient: 20% to 50% ethyl acetate in heptane), to afford trans-N-[4-(4-bromophenoxy)tetrahydrofuran-3-yl]propane-2-sulfonamide. Yield: 626 mg, 1.72 mmol, 91%. LCMS m/z 361.9 (M−1). 1H NMR (400 MHz, CDCl3) δ 1.38 (d, J=6.9 Hz, 3H), 1.40 (d, J=6.8 Hz, 3H), 3.19 (septet, J=6.8 Hz, 1H), 3.82 (br d, J=8.0, 1H), 3.91 (dd, J=10.6, 1.7 Hz, 1H), 4.02-4.08 (m, 2H), 4.24 (dd, J=10.5, 4.7 Hz, 1H), 4.85 (br d, J=4.7 Hz, 1H), 4.95 (br d, J=8.3 Hz, 1H), 6.88 (d, J=9.0 Hz, 2H), 7.40 (d, J=9.0 Hz, 2H). 13C NMR (100 MHz, CDCl3) δ 16.45, 16.71, 54.14, 58.70, 71.45, 71.81, 82.07, 113.97, 117.20, 132.52, 155.75.

후처리

  1. customThe reaction was irradiated in a microwave reactor at 160° C. for 2 hours
  2. extractionThe reaction was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (Gradient: 20% to 50% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-7782dbbdb9ec4ab4bec4666b9d5beb56
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08686043B2

반응 노트

불러오는 중…