methyl 3-(azidomethyl)benzoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of methyl 3-(bromomethyl)benzoate in DMF (55 ml) under N2 was added sodium azide (10.39 g, 160 mmol) and stirred for 3 h. The solution was diluted with EtOAc, washed (water twice, then brine), dried (MgSO4), filtered, and concentrated to give the title compound. This material was used without further purification. MS (EI+) (m/z)=101.1 [M++1] washed (water twice brine), dried (MgSO4) filtered concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of methyl 3-(bromomethyl)benzoate in DMF (55 ml) under N2 was added sodium azide (10.39 g, 160 mmol) and stirred for 3 h. The solution was diluted with EtOAc, washed (water twice, then brine), dried (MgSO4), filtered, and concentrated to give the title compound. This material was used without further purification. MS (EI+) (m/z)=101.1 [M++1] washed (water twice brine), dried (MgSO4) filtered concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of methyl 3-(bromomethyl)benzoate in DMF (55 ml) under N2 was added sodium azide (10.39 g, 160 mmol) and stirred for 3 h. The solution was diluted with EtOAc, washed (water twice, then brine), dried (MgSO4), filtered, and concentrated to give the title compound. This material was used without further purification. MS (EI+) (m/z)=101.1 [M++1] washed (water twice brine), dried (MgSO4) filtered concentrated

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of methyl 3-(bromomethyl)benzoate (1.0 g, 4.4 mmol) in anhydrous DMF (10 mL) was added sodium azide (285 mg, 4.4 mmol). The resulting mixture was heated at 50° C. for 2 h, cooled, diluted with CHCl3 (100 mL), washed with water (5×50 mL), dried (MgSO4) and concentrated under reduced pressure to yield methyl 3-(azidomethyl)benzoate (0.84 g, quant.), which was used without purification. 1H-NMR (CDCl3): δ 8.01 (2H, m), 7.44-7.54 (2H, m), 4.42 (2H, s), 3.94 (3H, s). cooled washed with water (5×50 mL) dried (MgSO4) concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Treat a solution of 3-azidomethyl-benzoic acid methyl ester (0.4 g, 2.1 mmol) and 4-cyanophenylacetylene (0.25 g, 2.00 mmol) in 1 mL of dichloromethane with 1 mL of 0.1 M aqueous copper (II) sulfate solution and sodium ascorbate (0.06 g, 0.30 mmol). Stir at room temperature overnight, dilute the reaction with CH2Cl2 and wash 3 times with H2O. Dry the organic layer over sodium sulfate, filter and concentrate to afford a solid. Suspend the residue in diethyl ether and filter to give 0.53 g, 84% yield of 3-[4-(4-cyano-phenyl)-[1,2,3]triazol-1-ylmethyl]-benzoic acid methyl ester. dilute wash 3 times with H2O Dry the organic layer over sodium sulfate filter concentrate to afford a solid filter

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Add sodium azide (0.3 g, 4.8 mmol) to a solution of methyl 3-bromomethylbenzoate (1.00 g, 4.4 mmol) in 10 mL of dimethylacetamide. Stir at room temperature for several h, pour mixture into ice water and extract with EtOAc. Wash combined extracts 4 times with H2O, brine and dry over sodium sulfate. Filter the mixture and concentrate to afford 0.81 g, 97% yield of 3-azidomethyl-benzoic acid methyl ester as an oil. extract with EtOAc Wash dry over sodium sulfate Filter the mixture concentrate

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of methyl 3-(bromomethyl)benzoate (1.0 g, 4.4 mmol) in anhydrous DMF (10 mL) was added sodium azide (285 mg, 4.4 mmol). The resulting mixture was heated at 50° C. for 2 h, cooled, diluted with CHCl3 (100 mL), washed with water (5×50 mL), dried over MgSO4 and concentrated under reduced pressure to yield methyl 3-(azidomethyl)benzoate (0.84 g, quant.), which was used without purification. 1H-NMR (CDCl3): δ 8.01 (2H, m), 7.44–7.54 (2H, m), 4.42 (2H, s), 3.94 (3H, s). cooled washed with water (5×50 mL) dried over MgSO4 concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of methyl 3-(bromomethyl)benzoate in DMF (55 ml) under N2 was added sodium azide (10.39 g, 160 mmol) and stirred for 3 h. The solution was diluted with EtOAc, washed (water twice, then brine), dried (MgSO4), filtered, and concentrated to give the title compound. This material was used without further purification. MS (EI+) (m/z)=101.1 [M++1] washed (water twice brine), dried (MgSO4) filtered concentrated