Sodium Chloride → {4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-(2-methyl-pyrimidin-4-yl)-amine

HRID 1633714ノート

反応式

HRID 1633714 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][CH3:23])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Cl[C:34]1[CH:39]=[CH:38][N:37]=[C:36]([CH3:40])[N:35]=1.[Na+].[Cl-]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:23])[C:34]4[CH:39]=[CH:38][N:37]=[C:36]([CH3:40])[N:35]=4)=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 4244474-Chloro-2-methylpyrimidineHCID 18679487{4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methylamine

生成物 1

HCID 18679566{4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-(2-methyl-pyrimidin-4-yl)-amine収率 73.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

20 mg (0.064 mmol) {4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methylamine and 0.16 ml (0.96 mmol) N,N-diisopropyl ethyl amine in 1 ml of DMF were treated with 41 mg (0.32 mmol) 4-chloro-2-methylpyrimidine and stirred at 100° C. during 2 hours. After cooling to room temperature the mixture was treated with saturated aqueous NaCl and extracted three times with Et2O. Drying of the combined organic layers over Na2SO4, evaporation of the solvent and column chromatography on silica gel with EtOAc gave 19 mg (73%) {4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-(2-methyl-pyrimidin-4-yl)-amine as a light yellow oil, MS: 405 (MH+).

後処理

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted three times with Et2O
  3. dry with materialDrying of the combined organic layers over Na2SO4, evaporation of the solvent and column chromatography on silica gel with EtOAc

出典と根拠

ORDレコード
ord-e0519721f87541c1a968fdb9b4b9485a
出典データセット
uspto-grants-2003_01
特許番号
US06503907B2

反応ノート

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