methyl 4-bromo-3-formyl-1H-indole-2-carboxylate

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

Procedure: To a solution of EXAMPLE 107A (1.76 g) in N,N-dimethylformamide (10 mL) was added 1-(3-bromopropoxy)naphthalene (1.66 g) and Cs2CO3 (6.10 g). The mixture was stirred for 3 days at room temperature. The mixture was diluted with ethyl acetate (300 mL) and water (200 mL). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water (×3) and brine and dried over Na2SO4. After filtration, concentration of solvent gave crude product, which was purified by column chromatography (5% ethyl acetate in hexane). The aqueous layer was extracted with ethyl acetate The combined organic extracts were washed with water (×3) and brine dried over Na2SO4 After filtration, concentration of solvent gave crude product, which was purified by column chromatography (5% ethyl acetate in hexane)

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

Procedure: To a solution of EXAMPLE 107A (1.76 g) in N,N-dimethylformamide (10 mL) was added 1-(3-bromopropoxy)naphthalene (1.66 g) and Cs2CO3 (6.10 g). The mixture was stirred for 3 days at room temperature. The mixture was diluted with ethyl acetate (300 mL) and water (200 mL). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water (×3) and brine and dried over Na2SO4. After filtration, concentration of solvent gave crude product, which was purified by column chromatography (5% ethyl acetate in hexane). The aqueous layer was extracted with ethyl acetate The combined organic extracts were washed with water (×3) and brine dried over Na2SO4 After filtration, concentration of solvent gave crude product, which was purified by column chromatography (5% ethyl acetate in hexane)

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

Procedure: To a solution of methyl 4-bromo-1H-indole-2-carboxylate (4.09 g) in dichloromethane (60 mL) was added a mixture of POCl3 (3.7 g) and N,N-dimethylformamide (1.76 g). The mixture was stirred at reflux overnight. The mixture was diluted with ethyl acetate (300 mL) and 2M sodium acetate solution in water (200 mL). The mixture was stirred thoroughly for 1 hour. The aqueous layer was extracted with ethyl acetate. The combined extracts were washed with water (×3), brine and dried over Na2SO4. After filtration, concentration of the mixture gave the title compound, which was used in next step without purification. at reflux overnight The mixture was stirred thoroughly for 1 hour The aqueous layer was extracted with ethyl acetate The combined extracts were washed with water (×3), brine dried over Na2SO4 After filtration, concentration of the mixture

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

Procedure: To a solution of EXAMPLE 107A (1.76 g) in N,N-dimethylformamide (10 mL) was added 1-(3-bromopropoxy)naphthalene (1.66 g) and Cs2CO3 (6.10 g). The mixture was stirred for 3 days at room temperature. The mixture was diluted with ethyl acetate (300 mL) and water (200 mL). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water (×3) and brine and dried over Na2SO4. After filtration, concentration of solvent gave crude product, which was purified by column chromatography (5% ethyl acetate in hexane). The aqueous layer was extracted with ethyl acetate The combined organic extracts were washed with water (×3) and brine dried over Na2SO4 After filtration, concentration of solvent gave crude product, which was purified by column chromatography (5% ethyl acetate in hexane)

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

Procedure: To a solution of EXAMPLE 107A (1.76 g) in N,N-dimethylformamide (10 mL) was added 1-(3-bromopropoxy)naphthalene (1.66 g) and Cs2CO3 (6.10 g). The mixture was stirred for 3 days at room temperature. The mixture was diluted with ethyl acetate (300 mL) and water (200 mL). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water (×3) and brine and dried over Na2SO4. After filtration, concentration of solvent gave crude product, which was purified by column chromatography (5% ethyl acetate in hexane). The aqueous layer was extracted with ethyl acetate The combined organic extracts were washed with water (×3) and brine dried over Na2SO4 After filtration, concentration of solvent gave crude product, which was purified by column chromatography (5% ethyl acetate in hexane)

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

Procedure: To a solution of methyl 4-bromo-1H-indole-2-carboxylate (4.09 g) in dichloromethane (60 mL) was added a mixture of POCl3 (3.7 g) and N,N-dimethylformamide (1.76 g). The mixture was stirred at reflux overnight. The mixture was diluted with ethyl acetate (300 mL) and 2M sodium acetate solution in water (200 mL) The mixture was stirred thoroughly for 1 hour. The aqueous layer was extracted with ethyl acetate. The combined extracts were washed with water (×3), brine and dried over Na2SO4. After filtration, concentration of the mixture gave the title compound, which was used in next step without purification. at reflux overnight was stirred thoroughly for 1 hour The aqueous layer was extracted with ethyl acetate The combined extracts were washed with water (×3), brine dried over Na2SO4 After filtration, concentration of the mixture

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

Procedure: To a solution of methyl 4-bromo-1H-indole-2-carboxylate (4.09 g) in dichloromethane (60 mL) was added a mixture of POCl3 (3.7 g) and N,N-dimethylformamide (1.76 g). The mixture was stirred at reflux overnight. The mixture was diluted with ethyl acetate (300 mL) and 2M sodium acetate solution in water (200 mL). The mixture was stirred thoroughly for 1 hour. The aqueous layer was extracted with ethyl acetate. The combined extracts were washed with water (×3), brine and dried over Na2SO4. After filtration, concentration of the mixture gave the title compound, which was used in next step without purification. at reflux overnight The mixture was stirred thoroughly for 1 hour The aqueous layer was extracted with ethyl acetate The combined extracts were washed with water (×3), brine dried over Na2SO4 After filtration, concentration of the mixture

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

Procedure: To a solution of EXAMPLE 107A (1.76 g) in N,N-dimethylformamide (10 mL) was added 1-(3-bromopropoxy)naphthalene (1.66 g) and Cs2CO3 (6.10 g). The mixture was stirred for 3 days at room temperature. The mixture was diluted with ethyl acetate (300 mL) and water (200 mL). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water (×3) and brine and dried over Na2SO4. After filtration, concentration of solvent gave crude product, which was purified by column chromatography (5% ethyl acetate in hexane). The aqueous layer was extracted with ethyl acetate The combined organic extracts were washed with water (×3) and brine dried over Na2SO4 After filtration, concentration of solvent gave crude product, which was purified by column chromatography (5% ethyl acetate in hexane)

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

Procedure: To a solution of EXAMPLE 107A (1.76 g) in N,N-dimethylformamide (10 mL) was added 1-(3-bromopropoxy)naphthalene (1.66 g) and Cs2CO3 (6.10 g). The mixture was stirred for 3 days at room temperature. The mixture was diluted with ethyl acetate (300 mL) and water (200 mL). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water (×3) and brine and dried over Na2SO4. After filtration, concentration of solvent gave crude product, which was purified by column chromatography (5% ethyl acetate in hexane). The aqueous layer was extracted with ethyl acetate The combined organic extracts were washed with water (×3) and brine dried over Na2SO4 After filtration, concentration of solvent gave crude product, which was purified by column chromatography (5% ethyl acetate in hexane)

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

Procedure: To a solution of methyl 4-bromo-1H-indole-2-carboxylate (4.09 g) in dichloromethane (60 mL) was added a mixture of POCl3 (3.7 g) and N,N-dimethylformamide (1.76 g). The mixture was stirred at reflux overnight. The mixture was diluted with ethyl acetate (300 mL) and 2M sodium acetate solution in water (200 mL) The mixture was stirred thoroughly for 1 hour. The aqueous layer was extracted with ethyl acetate. The combined extracts were washed with water (×3), brine and dried over Na2SO4. After filtration, concentration of the mixture gave the title compound, which was used in next step without purification. at reflux overnight was stirred thoroughly for 1 hour The aqueous layer was extracted with ethyl acetate The combined extracts were washed with water (×3), brine dried over Na2SO4 After filtration, concentration of the mixture