Sodium borohydride → Ethyl 9-methyl-6-oxo-6,7,8,9-tetrahydropyrido[3',2':4,5]pyrrolo[1,2-a]pyrazine-2-carboxylate

HRID 1521719노트

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HRID 1521719 반응식
[C:1]([CH:3]([N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:13]=[C:8]2[CH:7]=[C:6]1[C:19]([O:21]CC)=O)[CH3:4])#[N:2].[BH4-].[Na+]>CO.C1COCC1>[CH3:4][CH:3]1[N:5]2[C:9]3[N:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=[CH:13][C:8]=3[CH:7]=[C:6]2[C:19](=[O:21])[NH:2][CH2:1]1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 67236322Diethyl 1-(1-cyanoethyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

생성물 1

HCID 67239191Ethyl 9-methyl-6-oxo-6,7,8,9-tetrahydropyrido[3',2':4,5]pyrrolo[1,2-a]pyrazine-2-carboxylate수율 43%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

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온도
60 °C

실험 절차

To a solution of diethyl 1-(1-cyanoethyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (807 mg, 2.56 mmol) in methanol/THF (14 mL, 1:1 v/v) at 0° C. is added sodium borohydride (968 mg, 25.6 mmol). The cold bath is removed and the reaction mixture is stirred for 30 min, at which point the reaction vessel is sealed and warmed to 60° C. After being stirred for 4 h, the mixture is cooled to room temperature and diluted with EtOAc. The organic phase is washed twice with 1Ma aqueous NaHSO4 and once with brine, is dried (Na2SO4), filtered and concentrated to provide the title compound as a light yellow solid (298 mg, 43%).

후처리

  1. customThe cold bath is removed
  2. customis sealed
  3. stirringAfter being stirred for 4 h
  4. temperaturethe mixture is cooled to room temperature
  5. additiondiluted with EtOAc
  6. washThe organic phase is washed twice with 1Ma aqueous NaHSO4 and once with brine
  7. dry with materialis dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7e952f4712b245a2bfa26928a3fa76cd
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073926B2

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