2-bromo-1-(1H-pyrrol-2-yl)ethanone

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

Procedure: 2-Bromo-1-(1H-pyrrol-2-yl)-ethanone (1.00 mmol, 0.19 g) in DME (3 ml) was treated with NaI (1.00 mmol, 0.15 g), and stirred vigorously for 30 minutes. A solution of diethyl malonate (1.50 mmol, 0.2 ml), NaH (1.00 mmol, 40 mg of 60% in oil), and DME (3 ml) was added to the bromide-NaI mixture, and held at room temperature overnight. Saturated aqueous ammonium chloride (10 ml) was added, then the mixture was extracted with ethyl acetate (2×25 ml). The combined organic extracts washed with brine (25 ml), then concentrated under reduced pressure. Purification of the residue by silica gel chromatography provided 0.21 g (79%) of 2-(1H-pyrrole-2-carbonyl)-malonic acid diethyl ester. 1H NMR (CDCl3) δ9.76 (1H, s), 7.04 (1H, dt, J=2.7, 1.3), 7.00 (1H, ddd, J=3.8, 2.4, 1.3), 6.30-6.26 (1H, m), 4.21 (4H, m), 4.02 (1H, t, J=7.3), 3.45 (2H, d, J=7.3), 1.25 (6H, t, J=7.1). held at room temperature overnight the mixture was extracted with ethyl acetate (2×25 ml) The combined organic extracts washed with brine (25 ml) concentrated under reduced pressure Purification of the residue by silica gel chromatography

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

Procedure: Crude 2-[1 -(trimethyl-silanyloxy)-vinyl]-1H-pyrrole was diluted with CH2Cl2 (10 ml), cooled to 0° C., and treated with N-bromosuccinimide (1.94 mmol, 0.35 g). The resulting mixture was put in a −20° C. freezer overnight. After warming to room temperature, the mixture was diluted with ethyl acetate (75 ml), washed with saturated aqueous sodium bicarbonate (2×20 ml), brine (2×20 ml), and the organics concentrated under reduced pressure. Purification of the residue by silica gel chromatography provided 0.29 g (80%) of 2-bromo-1-(1H-pyrrol-2-yl)-ethanone. 1H NMR (CDCl3) δ7.12 (1H, dt, J=2.7, 1.3), 7.02 (1H, ddd, J=3.8, 2.4, 1.3), 6.36-6.31 (1H, m), 4.27 (2H, s). After warming to room temperature washed with saturated aqueous sodium bicarbonate (2×20 ml), brine (2×20 ml) the organics concentrated under reduced pressure Purification of the residue by silica gel chromatography

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

Procedure: 2-Bromo-1-(1H-pyrrol-2-yl)-ethanone (1.00 mmol, 0.19 g) in DME (3 ml) was treated with NaI (1.00 mmol, 0.15 g), and stirred vigorously for 30 minutes. A solution of diethyl malonate (1.50 mmol, 0.2 ml), NaH (1.00 mmol, 40 mg of 60% in oil), and DME (3 ml) was added to the bromide-NaI mixture, and held at room temperature overnight. Saturated aqueous ammonium chloride (10 ml) was added, then the mixture was extracted with ethyl acetate (2×25 ml). The combined organic extracts washed with brine (25 ml), then concentrated under reduced pressure. Purification of the residue by silica gel chromatography provided 0.21 g (79%) of 2-(1H-pyrrole-2-carbonyl)-malonic acid diethyl ester. 1H NMR (CDCl3) δ 9.76 (1H, s), 7.04 (1H, dt, J=2.7, 1.3), 7.00 (1H, ddd, J=3.8, 2.4, 1.3), 6.30-6.26 (1H, m), 4.21 (4H, m), 4.02 (1H, t, J=7.3), 3.45 (2H, d, J=7.3), 1.25 (6H, t, J=7.1). held at room temperature overnight the mixture was extracted with ethyl acetate (2×25 ml) The combined organic extracts washed with brine (25 ml) concentrated under reduced pressure Purification of the residue by silica gel chromatography

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

Procedure: 2-Bromo-1-(1H-pyrrol-2-yl)-ethanone (1.00 mmol, 0.19 g) in DME (3 ml) was treated with NaI (1.00 mmol, 0.15 g), and stirred vigorously for 30 minutes. A solution of diethyl malonate (1.50 mmol, 0.2 ml), NaH (1.00 mmol, 40 mg of 60% in oil), and DME (3 ml) was added to the bromide-NaI mixture, and held at room temperature overnight. Saturated aqueous ammonium chloride (10 ml) was added, then the mixture was extracted with ethyl acetate (2×25 ml). The combined organic extracts washed with brine (25 ml), then concentrated under reduced pressure. Purification of the residue by silica gel chromatography provided 0.21 g (79%) of 2-(1H-pyrrole-2-carbonyl)-malonic acid diethyl ester. 1H NMR (CDCl3) δ 9.76 (1H, s), 7.04 (1H, dt, J=2.7, 1.3), 7.00 (1H, ddd, J=3.8, 2.4, 1.3), 6.30-6.26 (1H, m), 4.21 (4H, m), 4.02 (1H, t, J=7.3), 3.45 (2H, d, J=7.3), 1.25 (6H, t, J=7.1). held at room temperature overnight the mixture was extracted with ethyl acetate (2×25 ml) The combined organic extracts washed with brine (25 ml) concentrated under reduced pressure Purification of the residue by silica gel chromatography

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

Procedure: Crude 2-[1-(trimethyl-silanyloxy)-vinyl]-1H-pyrrole was diluted with CH2Cl2 (10 ml), cooled to 0° C., and treated with N-bromosuccinimide (1.94 mmol, 0.35 g). The resulting mixture was put in a −20° C. freezer overnight. After warming to room temperature, the mixture was diluted with ethyl acetate (75 ml), washed with saturated aqueous sodium bicarbonate (2×20 ml), brine (2×20 ml), and the organics concentrated under reduced pressure. Purification of the residue by silica gel chromatography provided 0.29 g (80%) of 2-bromo-1-(1H-pyrrol-2-yl)-ethanone. 1H NMR (CDCl3) δ 7.12 (1H, dt, J=2.7, 1.3), 7.02 (1H, ddd, J=3.8, 2.4, 1.3), 6.36-6.31 (1H, m), 4.27 (2H, s). After warming to room temperature washed with saturated aqueous sodium bicarbonate (2×20 ml), brine (2×20 ml) the organics concentrated under reduced pressure Purification of the residue by silica gel chromatography

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

Procedure: 2-Bromo-1-(1H-pyrrol-2-yl)-ethanone (1.00 mmol, 0.19 g) in DME (3 ml) was treated with NaI (1.00 mmol, 0.15 g), and stirred vigorously for 30 minutes. A solution of diethyl malonate (1.50 mmol, 0.2 ml), NaH (1.00 mmol, 40 mg of 60% in oil), and DME (3 ml) was added to the bromide-NaI mixture, and held at room temperature overnight. Saturated aqueous ammonium chloride (10 ml) was added, then the mixture was extracted with ethyl acetate (2×25 ml). The combined organic extracts washed with brine (25 ml), then concentrated under reduced pressure. Purification of the residue by silica gel chromatography provided 0.21 g (79%) of 2-(1H-pyrrole-2-carbonyl)-malonic acid diethyl ester. 1H NMR (CDCl3) δ9.76 (1H, s), 7.04 (1H, dt, J=2.7, 1.3), 7.00 (1H, ddd, J=3.8, 2.4, 1.3), 6.30-6.26 (1H, m), 4.21 (4H, m), 4.02 (1H, t, J=7.3), 3.45 (2H, d, J=7.3), 1.25 (6H, t, J=7.1). held at room temperature overnight the mixture was extracted with ethyl acetate (2×25 ml) The combined organic extracts washed with brine (25 ml) concentrated under reduced pressure Purification of the residue by silica gel chromatography

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

Procedure: Crude 2-[1 -(trimethyl-silanyloxy)-vinyl]-1H-pyrrole was diluted with CH2Cl2 (10 ml), cooled to 0° C., and treated with N-bromosuccinimide (1.94 mmol, 0.35 g). The resulting mixture was put in a −20° C. freezer overnight. After warming to room temperature, the mixture was diluted with ethyl acetate (75 ml), washed with saturated aqueous sodium bicarbonate (2×20 ml), brine (2×20 ml), and the organics concentrated under reduced pressure. Purification of the residue by silica gel chromatography provided 0.29 g (80%) of 2-bromo-1-(1H-pyrrol-2-yl)-ethanone. 1H NMR (CDCl3) δ7.12 (1H, dt, J=2.7, 1.3), 7.02 (1H, ddd, J=3.8, 2.4, 1.3), 6.36-6.31 (1H, m), 4.27 (2H, s). After warming to room temperature washed with saturated aqueous sodium bicarbonate (2×20 ml), brine (2×20 ml) the organics concentrated under reduced pressure Purification of the residue by silica gel chromatography

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

Procedure: 2-Bromo-1-(1H-pyrrol-2-yl)-ethanone (1.00 mmol, 0.19 g) in DME (3 ml) was treated with NaI (1.00 mmol, 0.15 g), and stirred vigorously for 30 minutes. A solution of diethyl malonate (1.50 mmol, 0.2 ml), NaH (1.00 mmol, 40 mg of 60% in oil), and DME (3 ml) was added to the bromide-NaI mixture, and held at room temperature overnight. Saturated aqueous ammonium chloride (10 ml) was added, then the mixture was extracted with ethyl acetate (2×25 ml). The combined organic extracts washed with brine (25 ml), then concentrated under reduced pressure. Purification of the residue by silica gel chromatography provided 0.21 g (79%) of 2-(1H-pyrrole-2-carbonyl)-malonic acid diethyl ester. 1H NMR (CDCl3) δ9.76 (1H, s), 7.04 (1H, dt, J=2.7, 1.3), 7.00 (1H, ddd, J=3.8, 2.4, 1.3), 6.30-6.26 (1H, m), 4.21 (4H, m), 4.02 (1H, t, J=7.3), 3.45 (2H, d, J=7.3), 1.25 (6H, t, J=7.1). held at room temperature overnight the mixture was extracted with ethyl acetate (2×25 ml) The combined organic extracts washed with brine (25 ml) concentrated under reduced pressure Purification of the residue by silica gel chromatography

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

Procedure: 2-Bromo-1-(1H-pyrrol-2-yl)-ethanone (1.00 mmol, 0.19 g) in DME (3 ml) was treated with NaI (1.00 mmol, 0.15 g), and stirred vigorously for 30 minutes. A solution of diethyl malonate (1.50 mmol, 0.2 ml), NaH (1.00 mmol, 40 mg of 60% in oil), and DME (3 ml) was added to the bromide-NaI mixture, and held at room temperature overnight. Saturated aqueous ammonium chloride (10 ml) was added, then the mixture was extracted with ethyl acetate (2×25 ml). The combined organic extracts washed with brine (25 ml), then concentrated under reduced pressure. Purification of the residue by silica gel chromatography provided 0.21 g (79%) of 2-(1H-pyrrole-2-carbonyl)-malonic acid diethyl ester. 1H NMR (CDCl3) δ 9.76 (1H, s), 7.04 (1H, dt, J=2.7, 1.3), 7.00 (1H, ddd, J=3.8, 2.4, 1.3), 6.30-6.26 (1H, m), 4.21 (4H, m), 4.02 (1H, t, J=7.3), 3.45 (2H, d, J=7.3), 1.25 (6H, t, J=7.1). held at room temperature overnight the mixture was extracted with ethyl acetate (2×25 ml) The combined organic extracts washed with brine (25 ml) concentrated under reduced pressure Purification of the residue by silica gel chromatography

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

Procedure: Crude 2-[1-(trimethyl-silanyloxy)-vinyl]-1H-pyrrole was diluted with CH2Cl2 (10 ml), cooled to 0° C., and treated with N-bromosuccinimide (1.94 mmol, 0.35 g). The resulting mixture was put in a −20° C. freezer overnight. After warming to room temperature, the mixture was diluted with ethyl acetate (75 ml), washed with saturated aqueous sodium bicarbonate (2×20 ml), brine (2×20 ml), and the organics concentrated under reduced pressure. Purification of the residue by silica gel chromatography provided 0.29 g (80%) of 2-bromo-1-(1H-pyrrol-2-yl)-ethanone. 1H NMR (CDCl3) δ 7.12 (1H, dt, J=2.7, 1.3), 7.02 (1H, ddd, J=3.8, 2.4, 1.3), 6.36-6.31 (1H, m), 4.27 (2H, s). After warming to room temperature washed with saturated aqueous sodium bicarbonate (2×20 ml), brine (2×20 ml) the organics concentrated under reduced pressure Purification of the residue by silica gel chromatography

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

Procedure: 2-Bromo-1-(1H-pyrrol-2-yl)-ethanone (1.00 mmol, 0.19 g) in DME (3 ml) was treated with NaI (1.00 mmol, 0.15 g), and stirred vigorously for 30 minutes. A solution of diethyl malonate (1.50 mmol, 0.2 ml), NaH (1.00 mmol, 40 mg of 60% in oil), and DME (3 ml) was added to the bromide-NaI mixture, and held at room temperature overnight. Saturated aqueous ammonium chloride (10 ml) was added, then the mixture was extracted with ethyl acetate (2×25 ml). The combined organic extracts washed with brine (25 ml), then concentrated under reduced pressure. Purification of the residue by silica gel chromatography provided 0.21 g (79%) of 2-(1H-pyrrole-2-carbonyl)-malonic acid diethyl ester. 1H NMR (CDCl3) δ9.76 (1H, s), 7.04 (1H, dt, J=2.7, 1.3), 7.00 (1H, ddd, J=3.8, 2.4, 1.3), 6.30-6.26 (1H, m), 4.21 (4H, m), 4.02 (1H, t, J=7.3), 3.45 (2H, d, J=7.3), 1.25 (6H, t, J=7.1). held at room temperature overnight the mixture was extracted with ethyl acetate (2×25 ml) The combined organic extracts washed with brine (25 ml) concentrated under reduced pressure Purification of the residue by silica gel chromatography

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

Procedure: Crude 2-[1 -(trimethyl-silanyloxy)-vinyl]-1H-pyrrole was diluted with CH2Cl2 (10 ml), cooled to 0° C., and treated with N-bromosuccinimide (1.94 mmol, 0.35 g). The resulting mixture was put in a −20° C. freezer overnight. After warming to room temperature, the mixture was diluted with ethyl acetate (75 ml), washed with saturated aqueous sodium bicarbonate (2×20 ml), brine (2×20 ml), and the organics concentrated under reduced pressure. Purification of the residue by silica gel chromatography provided 0.29 g (80%) of 2-bromo-1-(1H-pyrrol-2-yl)-ethanone. 1H NMR (CDCl3) δ7.12 (1H, dt, J=2.7, 1.3), 7.02 (1H, ddd, J=3.8, 2.4, 1.3), 6.36-6.31 (1H, m), 4.27 (2H, s). After warming to room temperature washed with saturated aqueous sodium bicarbonate (2×20 ml), brine (2×20 ml) the organics concentrated under reduced pressure Purification of the residue by silica gel chromatography