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Sodium Iodide → HCID 9953273, 화합물

HRID 1057621
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HRID 1057621 반응식
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[N:13]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:23])[C:7]2=1.Cl.[CH2:25]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29]Cl)[CH3:26].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C>[CH2:25]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29][O:23][C:8]1[C:7]2[C:6]3[C:14](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=3)[N:13]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1)[CH3:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

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HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 18671689HCID 18671689, 화합물

생성물 1

HCID 9953273HCID 9953273, 화합물수율 74.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

8-Fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-ol (0.0226 g, 0.073 mmol), 2-diethylaminoethylchloride hydrochloride (0.0202 g, 0.12 mmol), potassium carbonate (0.0330 g, 0.24 mmol), sodium iodide (0.0018 g, 0.012 mmol) and DMF (1 mL) are heated at 80° C. for 3 h. After the mixture had cooled, it is partitioned between water and ethyl acetate. The organic layer is dried over magnesium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (20 mL) using methanol/dichloromethane (2/98 and 4/96) to give 0.0222 g (74%) of the title compound; mp 59-60° C.; MS (ESI+) for C25H27F2N2O m/z 409.3 (M+H)+; 1H NMR (CDCl3) δ1.21, 2.87, 3.22, 4.45, 5.67, 6.74, 6.94, 7.02, 7.14, 7.39, 8.11. Anal. Calcd for C25H26F2N2O: C, 73.51; H, 6.41; N, 6.86. Found: C, 73.05; H, 6.61; N, 6.83.

후처리

  1. temperatureAfter the mixture had cooled
  2. customit is partitioned between water and ethyl acetate
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. concentrationconcentrated to an oil
  5. customThe oil is chromatographed on silica gel (20 mL)

출처 및 근거

ORD 기록
ord-ca411eeea855499193a14009d7f51832
출처 데이터셋
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06514968B1

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