Sodium Iodide → N,N-Diethyl-N-(2-{[6-fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-yl]oxy}ethyl)amine

HRID 1057633ノート

反応式

HRID 1057633 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:23])[C:5]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:6]1[C:5]2[C:4]3[C:12](=[CH:13][CH:14]=[C:2]([F:1])[CH:3]=3)[N:11]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH3:26]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 186716846-Fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-ol

生成物 1

HCID 18671674N,N-Diethyl-N-(2-{[6-fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-yl]oxy}ethyl)amine収率 61%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

6-Fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-ol (0.0584 g, 0.19 mmol), 2-diethylaminoethylchloride hydrochloride (0.0593 g, 0.35 mmol), potassium carbonate (0.0926 g, 0.63 mmol), sodium iodide (0.0061 g, 0.041 mmol) and DMF (2 mL) are heated at 85° C. for 3 h. After the mixture had cooled, it is partitioned between water and ethyl acetate. The combined organic layers are dried over magnesium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (50 mL) using methanol/dichloromethane (1/99) to give 0.0471 g (61%) of the title compound; mp 75-76° C.; MS (ESI+) for C25H26F2N2O m/z 409.3 (M+H)+; IR (drift) 1585, 1507, 1481, 1461, 1343, 1269, 1221, 1159, 1145, 871, 820, 799, 776, 739, 712 cm−1; 1H NMR (CDCl3) δ1.14, 2.73, 3.10, 4.33, 5.44, 6.69, 6.93, 7.04-7.18, 7.36, 8.03. Anal. Calcd for C25H26F2N2O: C, 73.51; H, 6.41; N, 6.86. Found:C, 73.30; H, 6.59; N, 6.77.

後処理

  1. temperatureAfter the mixture had cooled
  2. customit is partitioned between water and ethyl acetate
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. concentrationconcentrated to an oil
  5. customThe oil is chromatographed on silica gel (50 mL)

出典と根拠

ORDレコード
ord-64237b9df4584a5a88f63fa44e21e0e1
出典データセット
uspto-grants-2003_02
特許番号
US06514968B1

反応ノート

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