* 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.
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.25 h; Inert atmosphere Stage #2: at 20℃; Inert atmosphere
2-Methoxyethanol (0.820 mL, 10.39 mmol) was dissolved in THF (30 mL) and sodium hydride (60percent w/w) (0.416 g, 10.39 mmol) was added under nitrogen and left to stir at rt for 15 min. 4-bromo-2- chloropyridine (0.577 mL, 5.20 mmol) was added and the reaction was left stirring at rt overnight. More 2-methoxyethanol (0.410 mL, 5.19 mmol) was dissolved in 1 ,2-DME (10 mL) and sodium hydride (60percent w/w) (0.208 mg, 5.19 mmol) was added. The mixture was stirred under nitrogen at rt for 15 min then added to the reaction which was stirred at rt for 3 days. Water was added (40 mL) and the organic product was extracted with EtOAc and washed with brine, dried through a hydrophobic frit and concentrated in vacuo. The residue was purified by silica gel column chromatography [0-20percent EtOAc in cyclohexane] and fractions containing product were concentrated in vacuo to give the title compound as a colourless liquid (314 mg, 1.353 mmol, 26.0 percent yield). LCMS (2 min, Formic Acid): Rt = 0.93 min, MH+ = 232/234.
26%
Stage #1: With sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere Stage #2: at 20℃;
2-Methoxyethanol (0.820 mL, 10.39 mmol) was dissolved in THF (30 mL) and sodium hydride (60 percent w/w) (0.416 g, 10.39 mmol) was added under nitrogen and left to stir at rt for 15 min. 4-bromo-2- chloropyridine (0.577 mL, 5.20 mmol) was added and the reaction was left stirring at rt overnight. Further 2-methoxyethanol (0.410 mL, 5.19 mmol) was dissolved in 1 ,2-DME (10 mL) and sodium hydride (60 percent w/w) (0.208 mg, 5.19 mmol) was added. After 15 min at rt under nitrogen, this was added to the reaction mixture and left stirring at rt for 3 days. Water was added (40 mL) and the organic product was extracted with ethyl acetate. The organic layer was washed with brine, dried through a hydrophobic frit and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 0-20 percent ethyl acetate in cyclohexane. Fractions containing product were
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 0.5h;Microwave irradiation;
General procedure: A mixture of 4-bromo-2-ethoxypyridine (150 mg, 0.742 mmol), £>/s(pinacolato)diboron (754 mg, 2.97 mmol), PdCI2(dppf) (54.3 mg, 0.074 mmol) and potassium acetate (291 mg, 2.97 mmol) in 1 ,4- dioxane (3 ml.) was heated in a microwave at 1 10 C for 2 x 30 min. The reaction was diluted with EtOAc and filtered through a Celite column. The filtrate was evaporated to give a brown residue. This crude material was used in subsequent steps without further purification and the yield was assumed to be 100% (0.742 mmol, 185 mg).
2-Methoxyethanol (0.820 mL, 10.39 mmol) was dissolved in THF (30 mL) and sodium hydride (60% w/w) (0.416 g, 10.39 mmol) was added under nitrogen and left to stir at rt for 15 min. 4-bromo-2- chloropyridine (0.577 mL, 5.20 mmol) was added and the reaction was left stirring at rt overnight. More 2-methoxyethanol (0.410 mL, 5.19 mmol) was dissolved in 1 ,2-DME (10 mL) and sodium hydride (60% w/w) (0.208 mg, 5.19 mmol) was added. The mixture was stirred under nitrogen at rt for 15 min then added to the reaction which was stirred at rt for 3 days. Water was added (40 mL) and the organic product was extracted with EtOAc and washed with brine, dried through a hydrophobic frit and concentrated in vacuo. The residue was purified by silica gel column chromatography [0-20% EtOAc in cyclohexane] and fractions containing product were concentrated in vacuo to give the title compound as a colourless liquid (314 mg, 1.353 mmol, 26.0 % yield). LCMS (2 min, Formic Acid): Rt = 0.93 min, MH+ = 232/234.
26%
2-Methoxyethanol (0.820 mL, 10.39 mmol) was dissolved in THF (30 mL) and sodium hydride (60 % w/w) (0.416 g, 10.39 mmol) was added under nitrogen and left to stir at rt for 15 min. 4-bromo-2- chloropyridine (0.577 mL, 5.20 mmol) was added and the reaction was left stirring at rt overnight. Further 2-methoxyethanol (0.410 mL, 5.19 mmol) was dissolved in 1 ,2-DME (10 mL) and sodium hydride (60 % w/w) (0.208 mg, 5.19 mmol) was added. After 15 min at rt under nitrogen, this was added to the reaction mixture and left stirring at rt for 3 days. Water was added (40 mL) and the organic product was extracted with ethyl acetate. The organic layer was washed with brine, dried through a hydrophobic frit and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 0-20 % ethyl acetate in cyclohexane. Fractions containing product were
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 0.5h;Microwave irradiation;
A mixture of <strong>[1289131-55-0]4-bromo-2-(2-methoxyethoxy)pyridine</strong> (for a preparation see Intermediate 37, 306 mg, 1.319 mmol), 5/s(pinacolato)diboron (1004 mg, 3.96 mmol), PdCI2(dppf) (96 mg, 0.132 mmol) and potassium acetate (388 mg, 3.96 mmol) in 1 ,4-dioxane (10 mL) was heated in a microwave at 100C for 30 min. The reaction was diluted with ethyl acetate and filtered through a Celite column. The filtrate was evaporated to give 2-(2-methoxyethoxy)-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)pyridine as a brown residue. The yield was assumed to be 100 % (368 mg, 1.319 mmol). The material was used crude in the next stage without further purification. LCMS (2 min, Formic): Rt = 0.44 min, MH+ 198 (observed mass ion is consistent with hydrolysis to boronic acid under LCMS conditions).
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
Life Science
For Research Only
88K+ Compounds
Competitive Price
1-2 Day Shipping
