1,2-Dibromoethane → 6-(2-bromoethoxy)-N-cyclohexyl-4-methyl-1H-indole-2-carboxamide

HRID 62663ノート

反応式

HRID 62663 の反応式
[CH:1]1([NH:7][C:8]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[C:16]([CH3:19])[CH:15]=[C:14]([OH:20])[CH:13]=3)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:27][CH2:28][CH2:29]Br>C(#N)C.O>[Br:27][CH2:28][CH2:29][O:20][C:14]1[CH:13]=[C:12]2[C:17]([CH:18]=[C:10]([C:8]([NH:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[O:9])[NH:11]2)=[C:16]([CH3:19])[CH:15]=1

参加物

6

反応物 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 89995412N-cyclohexyl-6-hydroxy-4-methyl-1H-indole-2-carboxamide

生成物 1

HCID 899954026-(2-bromoethoxy)-N-cyclohexyl-4-methyl-1H-indole-2-carboxamide収率 21%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of N-cyclohexyl-6-hydroxy-4-methyl-1H-indole-2-carboxamide (I-9A-b: 0.7 g, 2.57 mmol) in acetonitrile (20 mL) was added Cs2CO3 (1.67 g, 5.14 mmol) cooled to 0° C. followed by 1,2-dibromoethane (1.1 mL, 12.86 mmol) dropwise. The reaction mixture was stirred at room temperature for 16 h, diluted with water (20 mL) and extracted with ethyl acetate (2×100 mL). The combined ethyl acetate layers were washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude compound was purified by column chromatography over silica gel (100-200 mesh) using a solvent gradient of 50% ethyl acetate in petroleum ether as eluent to afford 200 mg (21%) of 6-(2-bromoethoxy)-N-cyclohexyl-4-methyl-1H-indole-2-carboxamide (I-9A-c) as an off-white solid.

後処理

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washThe combined ethyl acetate layers were washed with brine (100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude compound was purified by column chromatography over silica gel (100-200 mesh)

出典と根拠

ORDレコード
ord-03f5978e40894be6a0f196790dd988c2
出典データセット
uspto-grants-2016_09
特許番号
US09447039B2

反応ノート

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