1H-pyrrole-2-carbonyl chloride

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: 40 ml of a solution of 45 (mmoles) of 2-chlorocarbonyl-1H-pyrrole in methylene chloride were added dropwise to a cold mixture of 4.3 ml of pyridine and 3.5 ml of methanol and the mixture was washed with water, then with 6 ml of N sodium hydroxide, and was extracted with methylene chloride. The organic phases were dried and concentrated to dryness and the residue was chromatographed over silica. Elution with a mixture of hexane and ethyl acetate (8-2) yielded 4.014 g of methyl 1H-pyrrole-2-carboxylate melting at ≃74° C. the mixture was washed with water with 6 ml of N sodium hydroxide, and was extracted with methylene chloride The organic phases were dried concentrated to dryness the residue was chromatographed over silica Elution with a mixture of hexane and ethyl acetate (8-2)

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

Procedure: Likewise, by the method of part B of this Preparation, pyrrole-2-carbonyl chloride, obtained as described by R. J. Boatman et al., in J. Org. Chem. 41, p. 3050 (1976), is converted into N,N-dimethylpyrrole-2-carbox-amide, m.p. 100.5°-102° C. obtained

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

Procedure: To a solution of 1H-pyrrole-2-carbonyl chloride (1.3 g, 10 mmol) (from Example 30) in DCM (20 mL) was added (S)-1-phenyl-ethylamine (1.4 g, 11.55 mmol) (Aldrich, Milwaukee, Wis.), followed by triethylamine (1.5 mL). The reaction was stirred at room temperature for overnight. The reaction was washed with 1N NaOH, water, brine, dried and concentrated to give 867 mg (40%) of 1H-pyrrole-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide. The reaction was washed with 1N NaOH, water, brine dried concentrated

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

Procedure: To a solution of 1H-pyrrole-2-carbonyl chloride (1.3 g, 10 mmol) (from Example 30) in DCM (20 mL) was added 3-fluoroaniline (1.2 g, 10.7 mmol) and triethylamine (1.5 mL). The mixture was stirred at room temperature for overnight. The reaction was washed with NaOH, water, brine, dried and concentrated to give 750 mg (37%) of 1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide. The reaction was washed with NaOH, water, brine dried concentrated

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

Procedure: To a solution of 1H-pyrrole-2-carbonyl chloride (1.3 g, 10 mmol) (from Example 30) in DCM (20 mL) was added 3-fluoroaniline (1.2 g, 10.7 mmol) and triethylamine (1.5 mL). The mixture was stirred at room temperature for overnight. The reaction was washed with NaOH, water, brine, dried and concentrated to give 750 mg (37%) of 1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide. The reaction was washed with NaOH, water, brine dried concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1H-pyrrole-2-carboxylic acid ethyl ester was prepared as follows: to a solution of 1H-pyrrole-2-carboxylic acid (10 mmol; Aldrich, Milwaukee, Wis.) in DCM (15 mL) was added oxalyl chloride (10 mmol) and 3 drops of DMF at 0° C. The solution was stirred at 0° C. for 30 minutes to form 1H-pyrrole-2-carbonyl chloride. Ethanol was added and the mixture was stirred at room temperature for 30 minutes. The mixture was concetrated to afford 1-carboxylic acid ethyl ester.

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

Procedure: A solution of pyrrole-2-carboxylic acid chloride (0.065 gm) in methylene chloride (0.5 ml) was added to a suspension of 4-amino-7-hydroxy-8-methyl-benzopyran-2-one (0.095 gm) in pyridine (2 ml). The suspension was heated at 70 for 10 mins. to obtain a homogeneous solution. The reaction mixture was then diluted with water, filtered and the solid was crystallized form dimethylformamide/water to afford the title compound. MS: m/e 284 (M+). The suspension was heated at 70 for 10 mins to obtain a homogeneous solution filtered the solid was crystallized form dimethylformamide/water

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: A solution of pyrrole-2-carboxylic acid chloride (0.065 gm) in methylene chloride (0.5 ml) was added to a suspension of 4-amino-7-hydroxy-8-methyl-benzopyran-2-one (0.095 gm) in pyridine (2 ml). The suspension was heated at 70 for 10 mins. to obtain a homogeneous solution. The reaction mixture was then diluted with water, filtered and the solid was crystallized form dimethylformamide/water to afford the title compound. MS: m/e 284 (M+). The suspension was heated at 70 for 10 mins to obtain a homogeneous solution filtered the solid was crystallized form dimethylformamide/water