5-bromofuran-2-carbonyl chloride

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

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-bromo-furan-2-carboxylic acid (38.2 g, 200 mmol) and thionylchloride (163.1 g, 1.37 mol) was stirred at 70° C. overnight. The mixture of 5-bromo-furan-2-carbonyl chloride was evaporated, solved in tetrahydrofuran (10 ml) and added to a mixture of hydrazine monohydrate (120.1 g, 2.4 mol), followed by stirring for 0.5 hours at <5° C. Water (50 ml) was added followed by filtration. The crystalline product was recrystallized from ethanol (125 ml, 96%). Yield 21.2 g (52%). was evaporated by stirring for 0.5 hours at <5° C followed by filtration The crystalline product was recrystallized from ethanol (125 ml, 96%)

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

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-bromo-2-furoic acid (2.1 g, 6.856 mmol) in THF (20 mL) was added oxalyl chloride (0.66 mL, 7.541 mmol). 2 drops of DMF were then added to the reaction mixture, with bubbles of CO observed to come out vigorously. Oxalyl chloride ((COCl)2) (0.1 mL) was then added. The reaction mixture was stirred at room temperature for 10 min and at 90° C. for 10 min. Solvent and excess (COCl)2 were taken off under vacuum to yield 5-bromo-furan-2-carbonyl chloride as a pale yellow crystalline solid.

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

Procedure: Using the procedure of Example 32, 1.91 g (10.0 mmoless) of commercially available 5-bromo-2-furancarboxylic acid was dissolved in 10 ml of thionyl chloride and heated to reflux under nitrogen for 1 hour and the acid chloride product was recovered. A 40 ml N,N-dimethylformamide solution of 1.75 g (8.3 mmoles) of 5-chloro-2-oxindole-1-carboxamide and 3.05 g (25 mmoles) of 4-(N,N-dimethylamino)pyridine was reacted with 2.09 g (10 mmoles) of 5-bromo-2-furan carbonyl chloride in 10 ml of N,N-dimethylformamide. After a reaction time of about 45 minutes, the mixture was acidified by pouring into 250 ml of 1N HCl. The product was recrystallized from acetic acid, washed with acetic acid, then hexane and dried overnight in vacuo at room temperature. The resulting product then was dried over refluxing isopropanol under high vacuum to yield 1.37 g of the title compound. heated to reflux under nitrogen for 1 hour the acid chloride product was recovered After a reaction time of about 45 minutes The product was recrystallized from acetic acid washed with acetic acid hexane and dried overnight in vacuo at room temperature The resulting product then was dried over refluxing isopropanol under high vacuum

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

Procedure: Using the procedure of Example 32, 1.91 g (10.0 mmoles) of commercially available 5-bromo-2-furan-carboxylic acid was dissolved in 10 ml of thionyl chloride and heated to reflux under nitrogen for 1 hour and the acid chloride product was recovered. A 40 ml N,N-dimethylformamide solution of 1.75 g (8.3 mmoles) of 5-chloro-2-oxindole-1-carboxamide and 3.05 g (25 mmoles) of 4-(N,N-dimethylamino)pyridine was reacted with 2.09 g (10 mmoles) of 5-bromo-2-furan carbonyl chloride in 10 ml of N,N-dimethylformamide. After a reaction time of about 45 minutes, the mixture was acidified by pouring into 250 ml of 1N HCl. The product was recrystallized from acetic acid, washed with acetic acid, then hexane and dried overnight in vacuo at room temperature. The resulting product then was dried over refluxing isopropanol under high vacuum to yield 1.37 g of the title compound. heated to reflux under nitrogen for 1 hour the acid chloride product was recovered After a reaction time of about 45 minutes The product was recrystallized from acetic acid washed with acetic acid hexane and dried overnight in vacuo at room temperature The resulting product then was dried over refluxing isopropanol under high vacuum

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

Procedure: Using the procedure of Example 32, 1.91 g (10.0 mmoless) of commercially available 5-bromo-2-furancarboxylic acid was dissolved in 10 ml of thionyl chloride and heated to reflux under nitrogen for 1 hour and the acid chloride product was recovered. A 40 ml N,N-dimethylformamide solution of 1.75 g (8.3 mmoles) of 5-chloro-2-oxindole-1-carboxamide and 3.05 g (25 mmoles) of 4-(N,N-dimethylamino)pyridine was reacted with 2.09 g (10 mmoles) of 5-bromo-2-furan carbonyl chloride in 10 ml of N,N-dimethylformamide. After a reaction time of about 45 minutes, the mixture was acidified by pouring into 250 ml of 1N HCl. The product was recrystallized from acetic acid, washed with acetic acid, then hexane and dried overnight in vacuo at room temperature. The resulting product then was dried over refluxing isopropanol under high vacuum to yield 1.37 g of the title compound. heated to reflux under nitrogen for 1 hour the acid chloride product was recovered After a reaction time of about 45 minutes The product was recrystallized from acetic acid washed with acetic acid hexane and dried overnight in vacuo at room temperature The resulting product then was dried over refluxing isopropanol under high vacuum

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

Procedure: Using the procedure of Example 32, 1.91 g (10.0 mmoles) of commercially available 5-bromo-2-furancarboxylic acid was dissolved in 10 ml of thionyl chloride and heated to reflux under nitrogen for 1 hour and the acid chloride product was recovered. A 40 ml N,N-dimethylformamide solution of 1.75 g (8.3 mmoles) of 5-chloro-2-oxindole-1-carboxamide and 3.05 g (25 mmoles) of 4-(N,N-dimethylamino)pyridine was reacted with 2.09 g (10 mmoles) of 5-bromo-2-furan carbonyl chloride in 10 ml of N,N-dimethylformamide. After a reaction time of about 45 minutes, the mixture was acidified by pouring into 250 ml of 1N HCl. The product was recrystallized from acetic acid, washed with acetic acid, then hexane and dried overnight in vacuo at room temperature. The resulting product then was dried over refluxing isopropanol under high vacuum to yield 1.37 g of the title compound. heated to reflux under nitrogen for 1 hour the acid chloride product was recovered After a reaction time of about 45 minutes The product was recrystallized from acetic acid washed with acetic acid hexane and dried overnight in vacuo at room temperature The resulting product then was dried over refluxing isopropanol under high vacuum

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

Procedure: Using the procedure of Example 32, 1.91 g (10.0 mmoles) of commercially available 5-bromo-2-furancarboxylic acid was dissolved in 10 ml of thionyl chloride and heated to reflux under nitrogen for 1 hour and the acid chloride product was recovered. A 40 ml N,N-dimethylformamide solution of 1.75 g (8.3 mmoles) of 5-chloro-2-oxindole-1-carboxamide and 3.05 g (25 mmoles) of 4-(N,N-dimethylamino)pyridine was reacted with 2.09 g (10 mmoles) of 5-bromo-2-furan carbonyl chloride in 10 ml of N,N-dimethylformamide. After a reaction time of about 45 minutes, the mixture was acidified by pouring into 250 ml of 1N HCl. The product was recrystallized from acetic acid, washed with acetic acid, then hexane and dried overnight in vacuo at room temperature. The resulting product then was dried over refluxing isopropanol under high vacuum to yield 1.37 g of the title compound. heated to reflux under nitrogen for 1 hour the acid chloride product was recovered After a reaction time of about 45 minutes The product was recrystallized from acetic acid washed with acetic acid hexane and dried overnight in vacuo at room temperature The resulting product then was dried over refluxing isopropanol under high vacuum

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-bromo-furan-2-carboxylic acid (38.2 g, 200 mmol) and thionylchloride (163.1 g, 1.37 mol) was stirred at 70° C. overnight. The mixture of 5-bromo-furan-2-carbonyl chloride was evaporated, solved in tetrahydrofuran (10 ml) and added to a mixture of hydrazine monohydrate (120.1 g, 2.4 mol), followed by stirring for 0.5 hours at <5° C. Water (50 ml) was added followed by filtration. The crystalline product was recrystallized from ethanol (125 ml, 96%). Yield 21.2 g (52%). was evaporated by stirring for 0.5 hours at <5° C followed by filtration The crystalline product was recrystallized from ethanol (125 ml, 96%)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-bromo-furan-2-carboxylic acid (38.2 g, 200 mmol) and thionylchloride (163.1 g, 1.37 mol) was stirred at 70° C. overnight. The mixture of 5-bromo-furan-2-carbonyl chloride was evaporated, solved in tetrahydrofuran (10 ml) and added to a mixture of hydrazine monohydrate (120.1 g, 2.4 mol), followed by stirring for 0.5 hours at <5° C. Water (50 ml) was added followed by filtration. The crystalline product was recrystallized from ethanol (125 ml, 96%). Yield 21.2 g (52%). was evaporated by stirring for 0.5 hours at <5° C followed by filtration The crystalline product was recrystallized from ethanol (125 ml, 96%)

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

Procedure: A solution of 22.6 g of 5-bromo-2-furancarboxylic acid chloride in 100 ml of methylene chloride was added dropwise within 20 minutes at 0°-8° to a solution, pre-cooled to 0°, of 11.0 g of monoacetyl-ethylenediamine in 250 ml of methylene chloride and 18 ml of triethylamine. The reaction mixture was stirred at room temperature overnight, suction filtered and washed with methylene chloride. There was obtained N-(2-acetamino ethyl)-5-bromo-2-furancarboxamide as pale beige crystals, m.p. 175°-176°. suction filtered washed with methylene chloride