ethyl 5-bromofuran-2-carboxylate

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:; See reaction.notes.procedure_details.

Procedure: To a solution of ethyl 5-bromofuran-2-carboxylate (150 mg, 0.69 mmol) in DME (5 mL) were added 4-fluoro-3-(trifluoromethyl)phenylboronic acid (171 mg, 0.82 mmol), 2M Na2CO3 (1.03 mL, 2.06 mol), and catalytic amounts of Pd(Ph3)4 (158 mg, 0.14 mmol). The reaction mixture was refluxed for 5 h, diluted with water and extracted with EtOAc. The extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel (EtOAc/n-Hex=1:5) to give title compound (174 mg, 70%). The reaction mixture was refluxed for 5 h extracted with EtOAc The extracts were washed with brine dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure The crude residue was purified by column chromatography on silica gel (EtOAc/n-Hex=1:5)

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

Procedure: To a solution of ethyl 5-bromofuran-2-carboxylate (100 mg, 0.46 mmol) in benzene (5 mL) were added 3,5-bis(trifluoromethyl)phenylboronic acid (141 mg, 0.55 mmol), 2M Na2CO3 (6860, 1.37 mmol), and catalytic amounts of Pd(PPh3)4 (106 mg, 0.09 mmol). The reaction mixture was refluxed for 6 hrs, diluted with water and extracted with EtOAc. The extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel (EtOAc/n-Hex=1:5) to give title compound (61 mg, 38%). The reaction mixture was refluxed for 6 hrs extracted with EtOAc The extracts were washed with brine dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure The crude residue was purified by column chromatography on silica gel (EtOAc/n-Hex=1:5)

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

Procedure: To a solution of ethyl 5-bromofuran-2-carboxylate (100 mg, 0.46 mmol) in benzene (5 mL) were added 3,5-bis(trifluoromethyl)phenylboronic acid (141 mg, 0.55 mmol), 2M Na2CO3 (6860, 1.37 mmol), and catalytic amounts of Pd(PPh3)4 (106 mg, 0.09 mmol). The reaction mixture was refluxed for 6 hrs, diluted with water and extracted with EtOAc. The extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel (EtOAc/n-Hex=1:5) to give title compound (61 mg, 38%). The reaction mixture was refluxed for 6 hrs extracted with EtOAc The extracts were washed with brine dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure The crude residue was purified by column chromatography on silica gel (EtOAc/n-Hex=1:5)

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

Procedure: Again using the general procedure of Example 11, but using instead 4,4-dimethyl-6-ethynylthiochroman and ethyl 5-bromo-2-furate, the title compound was synthesized.

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

Procedure: Again using the general procedure of Example 11, but using instead 4,4-dimethyl-6-ethynylthiochroman and ethyl 5-bromo-2-furate, the title compound was synthesized.

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

Procedure: Again using the general procedure of Example 11, but using instead 4,4-dimethyl-6-ethynylthiochroman and ethyl 5-bromo-2-furate, the title compound was synthesized.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the compound obtained in Example 29 (1) (0.5 g) in N,N-dimethylformamide (5 ml), trimethylsilylacetylene (0.65 ml), bistriphenylphosphine palladium dichloride (0.16 g), cuprous iodide (0.04 g) and triethylamine (0.64 ml) were added successively and the mixture was stirred in a sealed tube at 100° C. for 2 hours. After cooling, the reaction solution was poured into water, extracted with ethyl acetate, washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 0.3782 g of the desired product as a brown oil. After cooling extracted with ethyl acetate washed with a saturated aqueous NaCl solution dried over anhydrous sodium sulfate filtered concentrated under reduced pressure The resulting residue was separated

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

Procedure: To a solution of 2-bromo-5-carboxyfuran (10 g) in dimethyl sulfoxide (100 ml), potassium carbonate (7.96 g) was added at 15 to 30° C. and ethyl iodide (16.8 ml) was added dropwise thereto. The mixture was stirred for 15 hours. The reaction solution was then poured into water and extracted with chloroform. The organic layer was washed with water, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 11.34 g of the desired product as an oil. extracted with chloroform The organic layer was washed with water a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate filtered concentrated under reduced pressure The resulting residue was separated