Potassium Carbonate → diethyl 1-(1-cyanoethyl)-1H-indole-2,6-dicarboxylate

HRID 1710448ノート

反応式

HRID 1710448 の反応式
C([O-])([O-])=O.[K+].[K+].[CH2:7]([O:9][C:10]([C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:15]=2)=[O:11])[CH3:8].Br[CH:27]([CH3:30])[C:28]#[N:29]>CN(C=O)C>[CH2:7]([O:9][C:10]([C:12]1[N:13]([CH:27]([C:28]#[N:29])[CH3:30])[C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:15]=2)=[O:11])[CH3:8]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 1405382-BromopropionitrileHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate

生成物 1

HCID 67235490diethyl 1-(1-cyanoethyl)-1H-indole-2,6-dicarboxylate収率 64.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A mixture of K2CO3 (7.93 g, 57.0 mmol) and 1H-indole-2,6-dicarboxylic acid diethyl ester (5.0 g, 19.14 mmol) in DMF (30 mL) was stirred at room temperature for 0.5 h. Then 2-bromo-propionitrile (3.4 mL, 38.3 mmol) in DMF (10 mL) was added. The reaction was warmed to 80° C. and kept at this temperature for 6 h. Then the reaction was cooled down to the room temperature. Most of the DMF solvent was removed in vacuo and the crude residue was extracted several times with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated. The crude product was triturated with MeCN to give 3.9 g of 1-(cyano-methyl-methyl)-1H-indole-2,6-dicarboxylic acid diethyl ester as a white fluffy solid. The filtrate was concentrated and purification by silica gel chromatography provided 1.6 g of 1-(cyano-methyl-methyl)-1H-indole-2,6-dicarboxylic acid diethyl ester, yield 91%.

後処理

  1. temperatureThe reaction was warmed to 80° C.
  2. waitkept at this temperature for 6 h
  3. temperatureThen the reaction was cooled down to the room temperature
  4. customMost of the DMF solvent was removed in vacuo
  5. extractionthe crude residue was extracted several times with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe crude product was triturated with MeCN

出典と根拠

ORDレコード
ord-7abc3b1c62764aa3a202a7144780f25c
出典データセット
uspto-grants-2010_09
特許番号
US07790712B2

反応ノート

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