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2-chloro-6-[(2S)-2-(4-methylphenyl)pyrrolidin-1-yl]-4-(1-methyl-1H-pyrazol-4-yl)pyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
104 mg
With palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate In toluene at 100℃; for 9h; Inert atmosphere;
69.2 Step 2 Production of 2-chloro-6-[(2S)-2-(4-methylphenyl)pyrrolidin-1-yl]-4-(1-methyl-1H-pyrazol-4-yl)pyridine
Step 2 Production of 2-chloro-6-[(2S)-2-(4-methylphenyl)pyrrolidin-1-yl]-4-(1-methyl-1H-pyrazol-4-yl)pyridine [0311] 2 mL of toluene was added to 161 mg of 2,6-dichloro-4-(1-methyl-1H-pyrazol-4-yl)pyridine, 137 mg of (2S)-2-(4-methylphenyl)pyrrolidine, 57 mg of DPEphos, 102 mg of sodium tert-butoxide and 16 mg of palladium(II)acetate, and the mixture was degassed, and then was stirred at 100°C for 9 hours under an argon atmosphere. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water, and was dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the resulting residue was purified by silica gel column chromatography to obtain 104 mg of the objective compound as a colorless oil.
2-chloro-6-[(2S)-2-(4-methylphenyl)pyrrolidin-1-yl]pyrazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
148 mg
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 80℃; for 20h;
1.1 Step 1 Production of 2-chloro-6-[(2S)-2-(4-methylphenyl)pyrrolidin-1-yl]pyrazi ne
Step 1 Production of 2-chloro-6-[(2S)-2-(4-methylphenyl)pyrrolidin-1-yl]pyrazi ne [0131] 100 mg of (2S)-2-(4-methylphenyl)pyrrolidine and 102 mg of 2, 6-dichloropyrazine were dissolved in 2 mL of 1-butanol, and then the mixture was added with 130 µL of DIPEA, and stirred at 80°C for 20 hours. After the reaction mixture was cooled until room temperature, the solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 148 mg of the objective compound as a white amorphous.
tert-butyl 2-chloro-6-[(2S)-2-(4-methylphenyl)pyrrolidin-1-yl]pyridine-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
1.1 g
With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 100℃;
Step 1 Production of tert-butyl 2-chloro-6-[(2S)-2-(4-methylphenyl)pyrrolidin-1-yl]pyridi ne-4-carboxylate [0267] 1.5 g of <strong>[75308-46-2]ter<strong>[75308-46-2]t-butyl 2,6-dichloroisonicotinate</strong></strong> and 1.02 g of (S)-2-(4-methylphenyl)pyrrolidine were dissolved in 1-butanol, and 2.0 mL of DIPEA was added to the solution, and then the mixture was stirred at 100C over night. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography to obtain 1.1 g of the objective compound as a yellow oil.
tert-butyl (4-oxo-4-(p-tolyl)butyl)carbamate[ No CAS ]
[ 1217847-41-0 ]
[ 1227908-77-1 ]
Yield
Reaction Conditions
Operation in experiment
88 % ee
Stage #1: tert-butyl (4-oxo-4-(p-tolyl)butyl)carbamate With trifluoroacetic acid In dichloromethane for 3h; Inert atmosphere; Schlenk technique;
Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane; titanium(IV) isopropylate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-[bis[4-(trifluoromethyl)phenyl]phosphino]ferrocene; hydrogen; potassium iodide In tetrahydrofuran; toluene at 50℃; for 13h; Autoclave; Overall yield = 97 percent; Overall yield = 31.2 mg; enantioselective reaction;
2-Substituted Arylpyrrolidines (2): General Procedure
General procedure: The mixture of substrate 1 (0.2 mmol) and TFA (6 equiv) in CH2Cl2 was stirred under nitrogen for 3 h. After all the acid and solvent had been removed under vacuum, the obtained substance was transferred to a nitrogen-filled glovebox and dissolved in a mixed solvent of toluene/THF (5:1, 1 mL). Ti(OiPr)4 (0.24 mmol), DABCO (0.04 mmol), Ir-L9 (0.002 mmol) and KI (0.04 mmol) were added subsequently to the above solution. The total solution was made to 3.0 mL. The resulting vial was transferred to an autoclave, which was charged with 50 atm of H2, and stirred at 50 °C for 13 h. The solution was quenched with aqueous sodium bicarbonate solution. The organic phase was concentratedand the metal complex was removed by using a short silica plug to give the chiral 2-substituted arylpyrrolidines product, which was then converted into the corresponding trifluoroacetamide with trifluoroacetic anhydride and analysed by chiral HPLC to determinethe enantiomeric excess.
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