* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
To sealed tube was added 5-bromo-2-fluoropyridine (825 mg, 5.1 mmol), dimethylamine/water (7.0 mL, 33%) and THF (3.0 mL), then sealed and heated to 110 C overnight. The reaction mixture was cooled to RT and extracted with EA, the organic layers were combined and washed with brine, then dried over a2S04 and concentrated to give compound 2-dimethylamino-5- bromopyridine as yellow oil (880 mg, yield 86%). Coupling under standard conditions gave 127 mg from 300 mg of 6-methyl-N-{4-[4-(tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-l,3-thiazol- 2-yl}pyridin-2-amine, yellow solid, 43% yield.
75%
In tetrahydrofuran; at 100℃;Sealed tube;
To a sealed tube was added 5-bromo-2-fluoropyridine (2.0 g, 1 1 .36 mmol), dimethylamine (7.0 mL, 45.6 mmol) in water and tetrahydrofuran (3 mL) and the reaction was heated to 100 C overnight. The reaction mixture was cooled to room temperature and extracted with EtOAc (15 mL x 3), the organic layers were combined and washed with brine and dried over Na2S04, filtered and concentrated under reduced pressure to give 5-bromo-N,N-dimethylpyridin-2-amine (1 .7 g, 8.46 mmol, 75 % yield) as a white solid.
With palladium diacetate; tricyclohexylphosphine; In 1,2-dimethoxyethane; water; at 80℃;
A mixture of 5-bromo-2-fluoropyridine (435 mg, 2.5 mmol), cyclopropylboronic acid (260 mg, 3.0 mmol), potassium phosphate (1.27 g, 6.0 mmol), palladium (II) acetate (56 mg, 0.6 mmol) and tricyclohexyl phosphine (340 mg, 1.2 mmol) in 1,2- dimethoxyethane/water (10.0 mL/2.0 mL) was stirred at 80 C overnight. The mixture was cooled and concentrated to dryness. The residue was purified by flash chromatography (petroleum ether / ethyl acetate = 3/1) to afford 5-cyclopropyl-2- fluoropyridine (246 mg, 1.8 mmol, 72% yield) as yellow solid. LCMS: m/z = 138.1 [M+H]+, retention time = 2.25 min (Method A).
647 mg
With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 80℃; for 16h;Inert atmosphere;
5-Bromo-2-fluoro - pyridine (1.41 g, 8 mmol) and cyclopropyl boronicacid (1.37 g, 16 mmol) mixed in toluene / water (26 mL / 1.3 mL), to which was added potassium phosphate (7.46 Under g, 28 mmol), argon was added theretopalladium acetate (90 mg, 0.4 mmol) and tricyclohexylphosphine (224 mg, 0.8mmol), the mixture was heated to 80 C the reaction 16h. After completion of the reaction by TLC, cooled to room temperature,water was added thereto, extracted with ethyl acetate, the organic phase wasdried over anhydrous sodium sulfate, filtered, and the solvent was evaporatedto dryness, purified by silica gel column chromatography to give 5-cyclopropyl-2-fluoro- pyridine (yellow oil, 647 mg).
5-bromo-2-[3-(1-pyrrolidinyl)propoxy]pyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83%
Sodium hydride (0.591g, 14.77mmol) was added portionwise to a solution of 3-(pyrrolidin- l-yl)propan-l-ol (1.615g, 12.50mmol) in THF (20mL) at to 0°C then stirred at ambient temperature for 30 minutes. 5-Bromo-2-fluoropyridine (2g, 11.36mmol) was added and the resulting mixture stirred at ambient temperature for 2 h before being quenched by the addition of a sat. aqueous solution of ammonium chloride. The moisture was extracted with EtOAc (2 x lOOmL), the organic layer dried over Na2SC>4, filtered and evaporated to afford pale yellow solid. The crude product was purified by FCC, elution gradient 0 to 10percent MeOH in DCM, to afford the desired material (2.70g, 83percent) as a yellow solid.
83%
Sodium hydride (0.59 1 g, 14.77 mmol) was added portionwise to a solution of 3- (pyrrolidin-1-yl)propan-1-ol(1.615 g, 12.50 mmol) in THF (20 mL) at to 0°C then stirred at ambient temperature for 30 minutes. 5-Bromo-2-fluoropyridine (2 g, 11.36 mmol) wasadded and the resulting mixture stirred at ambient temperature for 2 h before being quenched by the addition of a saturated aqueous solution of ammonium chloride. The mixture was extracted with EtOAc (2 x 100 mL), the organic layer dried over Na2SO4, filtered and evaporated to afford pale yellow solid. The crude product was purified byFCC, elution gradient 0 to 10percent MeOH in DCM, to afford the desired material (2.70 g, 83percent) as a yellow solid. Mass Spectrum: m/z (ES+)[M+H]+ = 285.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
