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

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 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 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:

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

Procedure: The preparation is carried out as in Example 1.1, from 20 g (79 mmol) of methyl 4-bromo-1H-indole-2-carboxylate, from 3.8 g of 60% sodium hydride and from 6 ml of iodomethane. After reaction, the solvent is evaporated under reduced pressure and the residue is taken up in water. The mixture is extracted with ethyl acetate. The organic phase is dried and the solvent is evaporated under reduced pressure. The product is dried under reduced pressure. 20.6 g (77 mmol) of solid are obtained. After reaction the solvent is evaporated under reduced pressure The mixture is extracted with ethyl acetate The organic phase is dried the solvent is evaporated under reduced pressure The product is dried under reduced pressure

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

Procedure: A solution of 116 g (0.41 mol) of methyl 2-azido-3-(2-bromophenyl)prop-2-enoate in 1.5 l of toluene is added dropwise over 4 h, with mechanical stirring, to a solution of 2 l of toluene heated to reflux and reflux is maintained for an additional 1 h. The solvent is evaporated under reduced pressure and the residue is taken up in 2 l of cyclohexane. The precipitate is collected by filtration, washed with toluene and dried under reduced pressure 37.85 g (149 mmol) of product are isolated. The mother liquors are concentrated under reduced pressure and the residue is purified by chromatography on a column of silica gel. 12.2 g (48 mmol) of additional product are isolated. heated to reflux reflux is maintained for an additional 1 h The solvent is evaporated under reduced pressure The precipitate is collected by filtration washed with toluene are isolated The mother liquors are concentrated under reduced pressure the residue is purified by chromatography on a column of silica gel

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