Potassium Carbonate → 2-Methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]-3-nitro-pyridine
Reaction equation
Cl.Cl.[CH3:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C@H:9]1[CH2:13][CH2:12][NH:11][CH2:10]1.C([O-])([O-])=O.[K+].[K+].Cl[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([CH3:30])[N:22]=1.C([O-])(O)=O.[Na+]>CS(C)=O>[CH3:30][C:23]1[C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=[C:21]([N:11]2[CH2:12][CH2:13][C@@H:9]([N:5]3[CH2:6][CH2:7][CH2:8][C@@H:4]3[CH3:3])[CH2:10]2)[N:22]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of (2R,3′S)-2-methyl-[1,3′]bipyrrolidinyl dihydrochloride (1.59 g, 7 mmol) in DMSO (24 mL) was added K2CO3 (3.87 g, 28 mmol) and 2-chloro-6-methyl-5-nitropyridine (1.81 g, 10.5 mmol) and then heated to 90° C. for 8 hours. The reaction was cooled to rt and NaHCO3 (aq) (200 mL) was added. The solution was extracted with EtOAc (2×250 mL). The combined organic extracts were washed with NaHCO3 (aq) (200 mL), H2O (200 mL), and brine (150 mL), dried over K2CO3, filtered and concentrated to obtain a residue which was then purified by flash column chromatography (0% to 5% MeOH/CH2Cl2) to afford 2 g of the title compound.
Workup
- temperatureThe reaction was cooled to rt
- extractionThe solution was extracted with EtOAc (2×250 mL)
- washThe combined organic extracts were washed with NaHCO3 (aq) (200 mL), H2O (200 mL), and brine (150 mL)
- dry with materialdried over K2CO3
- filtrationfiltered
- concentrationconcentrated
- customto obtain a residue which
- customwas then purified by flash column chromatography (0% to 5% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-b2917dcf54ab4be38f963db57483515d
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796278B2
Reaction notes
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