Cesium carbonate → HCID 57586581, 화합물

HRID 420358노트

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HRID 420358 반응식
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][SH:21])[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2].[Br:30][C:31]1[CH:32]=[C:33]([N+]([O-])=O)[CH:34]=[C:35]([Br:37])[CH:36]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][S:21][C:33]2[CH:32]=[C:31]([Br:30])[CH:36]=[C:35]([Br:37])[CH:34]=2)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 2387111,3-dibromo-5-nitrobenzeneHCID 57586501HCID 57586501, 화합물

생성물 1

HCID 57586581HCID 57586581, 화합물수율 72%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

To a solution of 4-[2-(2-ethoxycarbonyl-ethyl)-3-(6-mercapto-hexyl)-phenoxy]-butyric acid ethyl ester (162 mg, 0.388 mmol) in DMSO (5 mL), 3,5-dibromonitrobenzene (129 mg, 0.46 mmol) and Cs2CO3 (150 mg, 0.46 mmol) were added and stirred at 90° C. for 3 hrs. At this time, the reaction mixture was diluted with EtOAc (200 mL) and washed with water (100 mL). The EtOAc layer was washed), brine and then dried over Na2SO4. This mixture was filtered and the filtrate was concentrated. The solvent was removed in vacuo to afford an oil. This oil was purified using FCC (15% EtOAc/Hex) to provide a colorless oil (180 mg, yield 72%). 1H NMR (CDCl3): □ 7.42 (s, 1H), 7.32 (s, 2H), 7.09 (dd, 1H), 6.75 (d, 1H), 6.69 (d, 1H), 4.14 (m, 4H), 3.99 (t, 2H), 2.98-2.89 (m, 4H), 2.64-2.46 (m, 6H), 2.13 (m, 2H), 1.67-1.39 (m, 8H), 1.27 (m, 6H).

후처리

  1. washwashed with water (100 mL)
  2. washThe EtOAc layer was washed), brine
  3. dry with materialdried over Na2SO4
  4. filtrationThis mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customThe solvent was removed in vacuo
  7. customto afford an oil
  8. customThis oil was purified

출처 및 근거

ORD 기록
ord-39450b04c3fd4f94bb56e2657a09fc82
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093385B2

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