Water → Ethyl 4-cyano-1H-indole-2-carboxylate

HRID 62650ノート

反応式

HRID 62650 の反応式
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:6]2.O.[CH3:17][N:18](C=O)C>>[C:17]([C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:6]2)#[N:18]

参加物

4

反応物 3

HCID 962WaterHCID 6228DimethylformamideHCID 10989255Ethyl 4-bromo-1H-indole-2-carboxylate

生成物 1

HCID 53419488Ethyl 4-cyano-1H-indole-2-carboxylate収率 82%

反応条件

温度
150 °C

実験手順

To a stirred solution of ethyl 4-bromo-1H-indole-2-carboxylate (500 mg, 1.86 mmol) in DMF (10 mL) was added Cu(I)CN (501 mg, 5.59 mmol) and heated to 150° C. for 24 h. The reaction mixture was cooled to room temperature, the water (25 mL) was added and the reaction mixture extracted with ethyl acetate (4×50 mL). The organic layer was washed with water (25 mL), brine (25 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure to get the crude product. The crude product was purified by column chromatography over silica gel (100-200 mesh) using a solvent gradient of 10% ethyl acetate in petroleum ether to afford 330 mg (82%) of ethyl 4-cyano-1H-indole-2-carboxylate (I-3a) as an off-white solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe reaction mixture extracted with ethyl acetate (4×50 mL)
  3. washThe organic layer was washed with water (25 mL), brine (25 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated under reduced pressure
  6. customto get the crude product
  7. customThe crude product was purified by column chromatography over silica gel (100-200 mesh)

出典と根拠

ORDレコード
ord-fe4c8cac623845d0b661876aba5915d8
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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