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

HRID 1748243노트

반응식

HRID 1748243 반응식
C([O-])([O-])=O.[K+].[K+].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:14]=2)[CH:9]=[C:8]1[C:21]([O:23][CH2:24][CH3:25])=[O:22].Br[CH:27]([CH3:30])[C:28]#[N:29]>CN(C=O)C>[C:28]([CH:27]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:14]=2)[CH:9]=[C:8]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:30])#[N:29]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1405382-BromopropionitrileHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate2회

생성물 1

HCID 67235490diethyl 1-(1-cyanoethyl)-1H-indole-2,6-dicarboxylate수율 91.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A mixture of K2CO3 (7.9 g, 57.4 mmol) and diethyl 1H-indole-2,6-dicarboxylate (Intermediate A, 5.0 g, 19.1 mmol) in DMF (30 mL) is stirred at room temperature for 30 min. A solution of 2-bromo-propionitrile (3.4 mL, 38.3 mmol) in DMF (10 mL) is added. The reaction mixture is warmed to 80° C. for 6 h and then cooled to room temperature and stirred for another 16 h. Solvent is removed and the residue is partitioned between EtOAc and water. The organic layer is separated, dried and concentrated to afford crude compound which is purified by flash column chromatography using EtOAc in hexanes followed by trituration with acetonitrile to afford the title compound (5.5 g, 91%).

후처리

  1. temperatureThe reaction mixture is warmed to 80° C. for 6 h
  2. temperaturecooled to room temperature
  3. stirringstirred for another 16 h
  4. customSolvent is removed
  5. customthe residue is partitioned between EtOAc and water
  6. customThe organic layer is separated
  7. customdried
  8. concentrationconcentrated
  9. customto afford crude compound which
  10. customis purified by flash column chromatography

출처 및 근거

ORD 기록
ord-b6d32dc7d089434fa5e652930a62abb3
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150577B2

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