1,2-diethoxyethane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 40 g (0.22 mol) of phenazine are dissolved in 500 ml of anhydrous 1,2-diethoxyethane at 80° C. under an argon atmosphere. 14 g of sodium are added. The reaction mixture is stirred vigorously under reflux at 120° C. for 24 hours and cooled to room temperature. A solution of 39 g (0.66 mol) of 1,2-propylene oxide in 50 ml of 1,2-diethoxyethane is poured into the resultant 5,10-disodium 5,10-dihydrophenazine suspension. After the reaction mixture has been stirred at room temperature for 1 hour and at 50° C. for 2 hours, the precipitate is removed by filtration. All the anhydrous 1,2-diethoxyethane is distilled off on a rotary evaporator and used for the further synthesis. The solid residue, together with filtered-off precipitate, is mixed with 500 ml of methanol, and the mixture is stirred for 30 minutes. The solution is then evaporated on a rotary evaporator and transferred into a separating funnel, chloroform is added, and the mixture is washed a number of times with water and dried using magnesium sulphate. After the solvent has been distilled off, the product is purified by chromatography (silica gel column; cyclohexane/dioxane=1/1) and recrystallized from 150 ml of an acetone/water (2/1) mixture. The yield of the pale-green crystals is 22.5 g. cooled to room temperature After the reaction mixture has been stirred at room temperature for 1 hour and at 50° C. for 2 hours the precipitate is removed by filtration All the anhydrous 1,2-diethoxyethane is distilled off on a rotary evaporator used for the further synthesis the mixture is stirred for 30 minutes The solution is then evaporated on a rotary evaporator transferred into a separating funnel chloroform is added the mixture is washed a number of times with water dried After the solvent has been distilled off the product is purified by chromatography (silica gel column; cyclohexane/dioxane=1/1) recrystallized from 150 ml of an acetone/water (2/1) mixture

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dichlorobis(tri-o-tolylphosphine)palladium (II) (0.87 g, 1.1 mmol) was added into a mixture of 7-bromo-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol (7.16 g, 22.1 mmol), tributyl(vinyl)tin (10.5 g, 33.25 mmol) and ethylene glycol diethyl ether (65 mL). The reaction mixture was stirred at 115° C. for 48 h, cooled to room temperature and treated with activated carbon. The mixture was filtered through MgSO4 and concentrated. Purification by flash chromatography, on acidic silica gel (hexanes/EtOAc/CH2Cl2 1/1/1), gave a white solid (4.35 g, 72% yield, m.p. 250-252° C.); MS m/e 272 (M+H)+. cooled to room temperature treated with activated carbon The mixture was filtered through MgSO4 concentrated Purification by flash chromatography

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dichlorobis(tri-o-tolylphosphine)palladium (II) (0.87 g, 1.1 mmol) was added into a mixture of 7-bromo-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol (7.16 g, 22.1 mmol), tributyl(vinyl)tin (10.5 g, 33.25 mmol) and ethylene glycol diethyl ether (65 mL). The reaction mixture was stirred at 115° C. for 48 h, cooled to room temperature and treated with activated carbon. The mixture was filtered through MgSO4 and concentrated. Purification by flash chromatography, on acidic silica gel (hexanes/EtOAc/CH2Cl2 1/1/1), gave a white solid (4.35 g, 72% yield, m.p. 250-252° C.); MS m/e 272 (M+H)+. cooled to room temperature treated with activated carbon The mixture was filtered through MgSO4 concentrated Purification by flash chromatography

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1,4-diazabicyclo[3.2.2]nonane (20.2 g, 160 mmol), 1-fluoro-4-nitrobenzene (17.5 ml, 163.3 mmol) and ethylene glycol diethyl ether (160 ml) was stirred at 135° C. for 18 hours. The mixture was cooled to room-temperature and diethyl ether (100 ml) was added. The mixture was filtered and the product was isolated by filtration. Yield 24.8 g (58%). Mp. 122-129° C. was added The mixture was filtered the product was isolated by filtration

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dichlorobis(tri-o-tolylphosphine)palladium (II) (0.87 g, 1.1 mmol) was added into a mixture of 7-bromo-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol (7.16 g, 22.1 mmol), tributyl(vinyl)tin (10.5 g, 33.25 mmol) and ethylene glycol diethyl ether (65 mL). The reaction mixture was stirred at 115° C. for 48 h, cooled to room temperature and treated with activated carbon. The mixture was filtered through MgSO4 and concentrated. Purification by flash chromatography, on acidic silica gel (hexanes/EtOAc/CH2Cl2 1/1/1), gave a white solid (4.35 g, 72% yield, m.p. 250–252° C.); MS m/e 272 (M+H)+. cooled to room temperature treated with activated carbon The mixture was filtered through MgSO4 concentrated Purification by flash chromatography

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dichlorobis(tri-o-tolylphosphine)palladium (II) (0.87 g, 1.1 mmol) was added into a mixture of 7-bromo-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol (7.16 g, 22.1 mmol) tributyl(vinyl)tin (10.5 g, 33.25 mmol) and ethylene glycol diethyl ether (65 mL). The reaction mixture was stirred at 115° C. for 48 h, cooled to room temperature and treated with activated carbon. The mixture was filtered through MgSO4 and concentrated. Purification by flash chromatography, on acidic silica gel (hexanes/EtOAc/CH2Cl2 1/1/1), gave a white solid (4.35 g, 72% yield, m.p. 250-252° C.); MS m/e 272 (M+H)+. cooled to room temperature treated with activated carbon The mixture was filtered through MgSO4 concentrated Purification by flash chromatography