pent-1-enylboronic acid

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

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester (65 mg, 0.2 mmol) in DMF (2 mL) were added Potassium carbonate (54 mg, 0.39 mmol), Tetrabutylammonium chloride (54 mg, 0.2 mmol), Palladium acetate (3.5 mg, 0.02 mmol) in DMF (5 mL) and 1-Penten-1-ylboronic acid, (26 mg, 0.23 mmol). The resulting mixture was stirred under microwave irradiation (160° C., 15 min), cooled to room temperature, filtered over silica, washed with water, dried over MgSO4 and concentrated. Column chromatography (silica gel, heptane/CH2Cl2: 4/6) afforded title compound as a slightly colorless oil. cooled to room temperature filtered over silica washed with water dried over MgSO4 concentrated

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester (65 mg, 0.2 mmol) in DMF (2 mL) were added Potassium carbonate (54 mg, 0.39 mmol), Tetrabutylammonium chloride (54 mg, 0.2 mmol), Palladium acetate (3.5 mg, 0.02 mmol) in DMF (5 mL) and 1-Penten-1-ylboronic acid, (26 mg, 0.23 mmol). The resulting mixture was stirred under microwave irradiation (160° C., 15 min), cooled to room temperature, filtered over silica, washed with water, dried over MgSO4 and concentrated. Column chromatography (silica gel, heptane/CH2Cl2: 4/6) afforded title compound as a slightly colorless oil. cooled to room temperature filtered over silica washed with water dried over MgSO4 concentrated

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester (65 mg, 0.2 mmol) in DMF (2 mL) were added Potassium carbonate (54 mg, 0.39 mmol), Tetrabutylammonium chloride (54 mg, 0.2 mmol), Palladium acetate (3.5 mg, 0.02 mmol) in DMF (5 mL) and 1-Penten-1-ylboronic acid, (26 mg, 0.23 mmol). The resulting mixture was stirred under microwave irradiation (160° C., 15 min), cooled to room temperature, filtered over silica, washed with water, dried over MgSO4 and concentrated. Column chromatography (silica gel, heptane/CH2Cl2: 4/6) afforded title compound as a slightly colorless oil. cooled to room temperature filtered over silica washed with water dried over MgSO4 concentrated

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

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

Procedure: 4.0 g (18.9 mmol) of 6,7-difluoro-5-hydroxy-2-methylbenzofuran-4-carbaldehyde are stirred for 20 h at 90° C. together with 2.79 g (24.5 mmol) of 1-penteneboronic acid and 0.72 ml (3.73 mmol) of dibenzylamine in 95 ml of 1,4-dioxane. Water is added to the reaction mixture, which is then extracted with MTBE. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with water and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The crude product is firstly purified by column chromatography (SiO2, 1-chlorobutane) and subsequently crystallised from methanol, giving 4,5-difluoro-2-methyl-7-propyl-7H-furo[3,2-f]chromene as a yellow, crystalline solid. is then extracted with MTBE The organic phase is separated off the aqueous phase is extracted with MTBE The combined organic phases are washed with water and sat. sodium chloride soln The solution is dried concentrated to dryness The crude product is firstly purified by column chromatography (SiO2, 1-chlorobutane) subsequently crystallised from methanol

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

Procedure: 4.0 g (18.9 mmol) of 6,7-difluoro-5-hydroxy-2-methylbenzofuran-4-carbaldehyde are stirred for 20 h at 90° C. together with 2.79 g (24.5 mmol) of 1-penteneboronic acid and 0.72 ml (3.73 mmol) of dibenzylamine in 95 ml of 1,4-dioxane. Water is added to the reaction mixture, which is then extracted with MTBE. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with water and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The crude product is firstly purified by column chromatography (SiO2, 1-chlorobutane) and subsequently crystallised from methanol, giving 4,5-difluoro-2-methyl-7-propyl-7H-furo[3,2-f]chromene as a yellow, crystalline solid. is then extracted with MTBE The organic phase is separated off the aqueous phase is extracted with MTBE The combined organic phases are washed with water and sat. sodium chloride soln The solution is dried concentrated to dryness The crude product is firstly purified by column chromatography (SiO2, 1-chlorobutane) subsequently crystallised from methanol

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester (65 mg, 0.2 mmol) in DMF (2 mL) were added Potassium carbonate (54 mg, 0.39 mmol), Tetrabutylammonium chloride (54 mg, 0.2 mmol), Palladium acetate (3.5 mg, 0.02 mmol) in DMF (5 mL) and 1-Penten-1-ylboronic acid, (26 mg, 0.23 mmol). The resulting mixture was stirred under microwave irradiation (160° C., 15 min), cooled to room temperature, filtered over silica, washed with water, dried over MgSO4 and concentrated. Column chromatography (silica gel, heptane/CH2Cl2: 4/6) afforded title compound as a slightly colorless oil. cooled to room temperature filtered over silica washed with water dried over MgSO4 concentrated

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

Procedure: To a mixture of 1-(4-chlorophenyl)-1-cyclohexanecarbonitrile (100 mg, 0.455 mmol) and 1-pentenylboronic acid (104 mg, 0.910 mmol) in tetrahydrofuran (2 ml) and 1 M potassium carbonate (1.5 ml, 1.500 mmol) was added 1,1′-bis(di t-butylphosphino)ferrocene palladium dichloride (10 mg, 0.056 mmol). The mixture was microwaved at 100° C. in a sealed tube for 20 min, at which point LC/MS analysis showed a new peak. The reaction mixture was diluted with 10 mL of EtOAc and 10 mL of saturated aqueous NaHCO3. The phases were separated and the aqueous phase was extracted with 10 mL of EtOAc. The combined organics were washed with 10 mL of brine, dried (Na2SO4), and concentrated. The residue was purified by flash chromatography on a Biotage Horizon, 25M column, eluting with 1 CV of 100% hexanes followed by a gradient of 0 to 100% EtOAc in hexanes over 10 CV to provide the desired product 1-{4-[(1E)-pent-1-en-1-yl]phenyl}cyclohexanecarbonitrile (83 mg, 0.328 mmol, 72.0% yield). To a 0° C. solution of 1-{4-[(1E)-pent-1-en-1-yl]phenyl}cyclohexanecarbonitrile (75 mg, 0.296 mmol) in tetrahydrofuran (2 ml) was added 1.0 M lithium aluminum hydride in ether (1 ml, 1.000 mmol). The mixture was allowed to warm to room temperature and stirred at this temperature overnight, at which point LC/MS analysis showed complete disappearance of the starting nitrile. The mixture was recooled to 0° C. and quenched by dropwise addition of 30 μl of water, 30 μl of 15% NaOH, and 80 μl of water. The mixture was stirred for 30 min at room temperature, and then filtered, washing the solids liberally with ether. The filtrate was concentrated to provide the title compound (78 mg, 0.303 mmol, 102% yield). Mass spectrum (ESI) 258.0 (M+1). The mixture was microwaved at 100° C. in a sealed tube for 20 min, at which point LC/MS analysis The phases were separated the aqueous phase was extracted with 10 mL of EtOAc The combined organics were washed with 10 mL of brine dried (Na2SO4) concentrated The residue was purified by flash chromatography on a Biotage Horizon, 25M column eluting with 1 CV of 100% hexanes

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester (65 mg, 0.2 mmol) in DMF (2 mL) were added Potassium carbonate (54 mg, 0.39 mmol), Tetrabutylammonium chloride (54 mg, 0.2 mmol), Palladium acetate (3.5 mg, 0.02 mmol) in DMF (5 mL) and 1-Penten-1-ylboronic acid, (26 mg, 0.23 mmol). The resulting mixture was stirred under microwave irradiation (160° C., 15 min), cooled to room temperature, filtered over silica, washed with water, dried over MgSO4 and concentrated. Column chromatography (silica gel, heptane/CH2Cl2: 4/6) afforded title compound as a slightly colorless oil. cooled to room temperature filtered over silica washed with water dried over MgSO4 concentrated

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester (65 mg, 0.2 mmol) in DMF (2 mL) were added Potassium carbonate (54 mg, 0.39 mmol), Tetrabutylammonium chloride (54 mg, 0.2 mmol), Palladium acetate (3.5 mg, 0.02 mmol) in DMF (5 mL) and 1-Penten-1-ylboronic acid, (26 mg, 0.23 mmol). The resulting mixture was stirred under microwave irradiation (160° C., 15 min), cooled to room temperature, filtered over silica, washed with water, dried over MgSO4 and concentrated. Column chromatography (silica gel, heptane/CH2Cl2: 4/6) afforded title compound as a slightly colorless oil. cooled to room temperature filtered over silica washed with water dried over MgSO4 concentrated