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Iodine → HCID 86704621, 화합물

HRID 1508571
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HRID 1508571 반응식
N[C:2]1[CH:3]=[C:4]([C:9]2[C:10]([CH2:17][N:18]3[C@@H:22]([CH3:23])[C@@H:21]([C:24]4[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=4)[O:20][C:19]3=[O:38])=[N:11][C:12]([S:15][CH3:16])=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].N(OCCCCC)=O.[I:47]I>C(Cl)(Cl)Cl.C(Cl)Cl>[F:35][C:34]([F:37])([F:36])[C:26]1[CH:25]=[C:24]([C@H:21]2[O:20][C:19](=[O:38])[N:18]([CH2:17][C:10]3[C:9]([C:4]4[CH:5]=[CH:6][C:7]([F:8])=[C:2]([I:47])[CH:3]=4)=[CH:14][N:13]=[C:12]([S:15][CH3:16])[N:11]=3)[C@H:22]2[CH3:23])[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=1
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참가 물질

6

반응물 3

HCID 807IodineHCID 10026Pentyl nitriteHCID 86704619HCID 86704619, 화합물

생성물 1

HCID 86704621HCID 86704621, 화합물

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

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온도
80 °C

실험 절차

A mixture of the title compound from Step A (2.1 g, 3.75 mmol), n-pentyl nitrite (0.66 g, 5.62 mmol) and I2 (1.24 g, 4.87 mmol) in chloroform (20 mL) was stirred at 80° C. for 1 h. The mixture was cooled, and the solvent was diluted with CH2Cl2. The mixture was washed with Na2S2O3 (5 mL), and with brine (5 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40M, eluting with EtOAc/hexane (10/90) to give the title compound as a yellow gum. 1H NMR (CDCl3, 500 MHz) δ 8.41 (s, 1H), 7.92 (s, 1H), 7.78 (s, 2H), 7.77 (m, 1H), 7.35 (m, 1H), 7.22 (m, 1H), 5.76 (d, J=8.5 Hz, 1H), 4.91 (d, J=17 Hz, 1H), 4.45 (m, 1H), 4.06 (d, J=17.5 Hz, 1H), 2.64 (s, 3H), 0.76 (d, J=7 Hz, 3H). LCMS=672.1 (M+H)+.

후처리

  1. temperatureThe mixture was cooled
  2. washThe mixture was washed with Na2S2O3 (5 mL)
  3. dry with materialwith brine (5 mL), dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel Biotage 40M
  7. washeluting with EtOAc/hexane (10/90)

출처 및 근거

ORD 기록
ord-4124e88bc6ed4498a17fa3e80beefa65
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09221834B2

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