methyl 6-chloro-7-fluoro-1H-indole-2-carboxylate

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

Procedure: A stirred solution of methyl 6-chloro-7-fluoroindole-2-carboxylate (2.3 g, 10 mmol), tetrahydrofuran (20 mL) and aqueous sodium hydroxide solution (2 N, 20 mL) was heated under reflux for 16 h. The mixture was cooled to room temperature and partitioned between aqueous sulfiuric acid (2 M, 30 mL) and ethyl acetate (3×30 mL). The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to give the product (2.1 g, 98% yield) as a white solid: IR νmax (Nujol)/cm−1 1681, 1557, 1263, 1206, 926 and 840; NMR δH (400 MHz, DMSO-d6) 7.01-7.12 (2H, m) and 7.31-7.34 (1H, m). under reflux for 16 h partitioned between aqueous sulfiuric acid (2 M, 30 mL) and ethyl acetate (3×30 mL) The combined organic extracts were dried (magnesium sulfate) concentrated in vacuo

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

Procedure: A stirred solution of methyl 6-chloro-7-fluoroindole-2-carboxylate (2.3 g, 10 mmol), tetrahydrofuran (20 mL) and aqueous sodium hydroxide solution (2 N, 20 mL) was heated under reflux for 16 h. The mixture was cooled to room temperature and partitioned between aqueous sulfiuric acid (2 M, 30 mL) and ethyl acetate (3×30 mL). The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to give the product (2.1 g, 98% yield) as a white solid: IR νmax (Nujol)/cm−1 1681, 1557, 1263, 1206, 926 and 840; NMR δH (400 MHz, DMSO-d6) 7.01-7.12 (2H, m) and 7.31-7.34 (1H, m). under reflux for 16 h partitioned between aqueous sulfiuric acid (2 M, 30 mL) and ethyl acetate (3×30 mL) The combined organic extracts were dried (magnesium sulfate) concentrated in vacuo

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

Procedure: A solution of methyl 2-azido-3-(4-chloro-3-fluorophenyl)propenoate (15.08 g, 59 mmol) in xylene (200 mL) was added dropwise to stirred xylene (1 L) under reflux. The mixture was stirred for 3 h, cooled to room temperature, concentrated in vacuo and purified by column chromatography [SiO2; isopropyl ether-hexane (5:2)] to give the product (2.3 g, 17% yield) as a colourless solid: IR νmax (Nujol)/cm−1 3298, 1709, 1460, 1377, 1204 and 737; NMR δH (400 MHz, CDCl3) 3.85 (3H, s) 7.09-7.15 (1H, m) 7.21 (1H, m) 7.38 (1H, m) and 9.05 (1H, brs). under reflux concentrated in vacuo purified by column chromatography [SiO2; isopropyl ether-hexane (5:2)]

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

Procedure: A stirred solution of methyl 6-chloro-7-fluoroindole-2-carboxylate (2.3 g, 10 mmol), tetrahydrofuran (20 mL) and aqueous sodium hydroxide solution (2 N, 20 mL) was heated under reflux for 16 h. The mixture was cooled to room temperature and partitioned between aqueous sulfiuric acid (2 M, 30 mL) and ethyl acetate (3×30 mL). The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to give the product (2.1 g, 98% yield) as a white solid: IR νmax (Nujol)/cm−1 1681, 1557, 1263, 1206, 926 and 840; NMR δH (400 MHz, DMSO-d6) 7.01-7.12 (2H, m) and 7.31-7.34 (1H, m). under reflux for 16 h partitioned between aqueous sulfiuric acid (2 M, 30 mL) and ethyl acetate (3×30 mL) The combined organic extracts were dried (magnesium sulfate) concentrated in vacuo

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

Procedure: A solution of methyl 2-azido-3-(4-chloro-3-fluorophenyl)propenoate (15.08 g, 59 mmol) in xylene (200 mL) was added dropwise to stirred xylene (1 L) under reflux. The mixture was stirred for 3 h, cooled to room temperature, concentrated in vacuo and purified by column chromatography [SiO2; isopropyl ether-hexane (5:2)] to give the product (2.3 g, 17% yield) as a colourless solid: IR νmax (Nujol)/cm−1 3298, 1709, 1460, 1377, 1204 and 737; NMR δH (400 MHz, CDCl3) 3.85 (3H, s) 7.09-7.15 (1H, m) 7.21 (1H, m) 7.38 (1H, m) and 9.05 (1H, brs). under reflux concentrated in vacuo purified by column chromatography [SiO2; isopropyl ether-hexane (5:2)]