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With potassium tert-butylate; In tetrahydrofuran; at 0℃;Inert atmosphere;
Example 19i2-(Benzyloxy)-4-bromopyridine4-Bromo-2-fluoropyridine (5.28 g, 30 mmol) and benzyl alcohol (3.24 g, 30.00 mmol) were dissolved in dry THF (50 mL) under an atmosphere of argon. The solution was cooled with an external ice/water bath and held at 0 0C. Potassium tert-butoxidc (3.37 g, 30.00 mmol) was added in portions (approx. 100 mg each) under efficient stirring over a period of 20 min. Stirring at 0 0C was continued for 60 min, whereafter the cooling bath was removed and the mixture was stirred at rt for 30 min. Water (5 mL) was added to the reaction mixture and most of the THF was evaporated under reduced pressure. The remaining mixture was partitioned between pentane (75 mL) and water (50 mL). The organic phase was separated, washed with water (2x25 mL), dried over MgSO4 and the solvents removed in vacuo to afford 7.86 g (99%) of the title compound.1H NMR (500 MHz, DMSO-J6) delta 8.10 (d, IH) 7.44 (d, 2H) 7.38 (t, 2H) 7.33 (t, IH) 7.25 (d, IH) 7.20 (s, IH) 5.36 (s, 2H).
dibenzo-18-crown-6; In toluene; for 3h;Dean-Stark conditions; Reflux;
Arene 1; 2-(Benzyloxy)-4-bromopyridine; To a solution of 4-bromo-2-fluoropyridine (1 eq.), benzyl alcohol (1.2 eq.) and dibenzo-18-crown-6 (0.05 eq.) in toluene (0.4 M) was added potassium hydroxide (2 eq.). A Dean-Stark apparatus was then attached and the reaction suspension was heated at reflux for 3 h. After cooling to RT, the reaction mixture was diluted with hexanes and then filtered through a pad of celite. Concentration of the filtrate in vacuo afforded a yellow oil. Purification of the crude product thus obtained by way of column chromatography (SiO2, 97:3 (v/v) Hex : Et2O) afforded the title compound as a colorless oil.
With potassium hydroxide;dibenzo-18-crown-6; In toluene; for 3h;Inert atmosphere; Reflux;
To a solution of 4-bromo-2-fluoropyridine (1 eq.), benzyl alcohol (1.2 eq.) and dibenzo-18-crown-6 (0.05 eq.) in toluene (0.4 M) was added potassium hydroxide (2 eq.). A Dean-Stark apparatus was then attached and the reaction suspension was heated at reflux for 3 h. After cooling to RT, the reaction mixture was diluted with hexanes and then filtered through a pad of celite. Concentration of the filtrate in vacuo afforded a yellow oil. Purification of the crude product thus obtained by way of column chromatography (SiO2, 97:3 (v/v) Hex : Et2O) afforded the title compound as a colorless oil.
Step 1 To a mixture of 2,2-diethoxyethanol (22.87 g, 170 mmol, 1.5 eq) and 4-bromo-2-fluoro-pyridine (20 g, 113.65 mmol, 1 eq) in acetonitrile (200 mL) was added cesium carbonate (74.06 g, 227 mmol, 2 eq) in one portion at 15 C. under nitrogen. The mixture was stirred at 90 C. for 3 hours. The mixture was cooled to 20 C. and filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (petroleum ether) to afford 4-bromo-2-(2,2-diethoxyethoxy)pyridine (22.8 g, 74.7 mmol, 66% yield) as a yellow oil.
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