Potassium Carbonate → Diethyl 1-(1-cyanoethyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

HRID 1521718노트

반응식

HRID 1521718 반응식
[NH:1]1[C:5]2=[N:6][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+].Br[CH:27]([CH3:30])[C:28]#[N:29]>CN(C=O)C>[C:28]([CH:27]([N:1]1[C:5]2=[N:6][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:30])#[N:29]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1405382-BromopropionitrileHCID 67236396Diethyl 1H-pyrrolo[2,3-B]pyridine-2,6-dicarboxylate2회

생성물 1

HCID 67236322Diethyl 1-(1-cyanoethyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate수율 43.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of diethyl 1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (Intermediate D, 1.55 g, 5.91 mmol) in DMF (15 mL) is added potassium carbonate (2.45 g, 17.7 mmol), and the mixture is stirred at room temperature for 20 min. 2-bromopropionitrile (1.05 mL, 11.8 mmol) is added, the mixture is warmed to 80° C., and is stirred overnight. After being cooled to room temperature, the mixture is poured onto H2O, and the aqueous layer is extracted with EtOAc (3×100 mL). The combined organic extracts are dried (MgSO4), filtered, and concentrated. The crude material is purified via flash column chromatography using a gradient elution of 10-50% ethyl acetate/hexanes to afford the title compound as a bright yellow solid (809 mg, 43%).

후처리

  1. temperaturethe mixture is warmed to 80° C.
  2. stirringis stirred overnight
  3. temperatureAfter being cooled to room temperature
  4. additionthe mixture is poured onto H2O
  5. extractionthe aqueous layer is extracted with EtOAc (3×100 mL)
  6. dry with materialThe combined organic extracts are dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material is purified via flash column chromatography
  10. washa gradient elution of 10-50% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-3cf1058b80164a44a93a0dcc074f5606
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073926B2

반응 노트

불러오는 중…