Sodium borohydride → Ethyl 9-methyl-6-oxo-6,7,8,9-tetrahydropyrido[3',2':4,5]pyrrolo[1,2-a]pyrazine-2-carboxylate
Reaction equation
[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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
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%).
Workup
- customThe cold bath is removed
- customis sealed
- stirringAfter being stirred for 4 h
- temperaturethe mixture is cooled to room temperature
- additiondiluted with EtOAc
- washThe organic phase is washed twice with 1Ma aqueous NaHSO4 and once with brine
- dry with materialis dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7e952f4712b245a2bfa26928a3fa76cd
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073926B2
Reaction notes
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