Triethylamine → (R)-methyl 2-(2-nitropyridin-3-ylamino)pent-4-ynoate

Reaction equation

F[C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:11][C@H:12]([CH2:17][C:18]#[CH:19])[C:13]([O:15][CH3:16])=[O:14].C(N(CC)CC)C>CN(C=O)C>[N+:8]([C:3]1[C:2]([NH:11][C@H:12]([CH2:17][C:18]#[CH:19])[C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=[CH:5][N:4]=1)([O-:10])=[O:9]

Participants

Procedure

To a mixture of 3-fluoro-2-nitropyridine (860 mg, 6.05 mmol) and (R)-methyl 2-aminopent-4-ynoate (1.924 g, 15.131 mmol) in DMF was added triethylamine (2.55 ml, 18.16 mmol) and the resulting solution was stirred over the weekend. The reaction mixture was quenched with sat. NaHCO3, extracted with EtOAc/hexane=2:1, washed with brine, dried over Na2SO4 and the solvent was evaporated. Flash chromatography (SiO2, DCM to DCM/EtOAc=3:1 to 2:1) afforded the title compound as a pale yellow solid.