2-iodobenzaldehyde

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:

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

実験手順: A suspension of pyridinium chlorochromate (8.28 g, 38.4 mmol) and dry celite (5.00 g) in dry dichloromethane was stirred at room temperature for 15 min. 2-Iodobenzyl alcohol (3.03 g, 12.9 mmol) in dry dichloromethane (50 ml) was added. The suspension was shielded from light and stirred at room temperature for 2 h after which it was diluted with ether, and filtered through celite. The cloudy brown filtrate was concentrated to a red-brown gummy solid which was dissolved in dichloromethane and passed through a short silica column, eluting with dichloromethane. The solution was concentrated to give 2-iodobenzaldehyde (19) as a pale yellow oil (2.87 g, 95%). dry celite (5.00 g) in dry dichloromethane stirred at room temperature for 2 h after which it filtered through celite The cloudy brown filtrate was concentrated to a red-brown gummy solid which was dissolved in dichloromethane eluting with dichloromethane The solution was concentrated

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

実験手順: Prepared from 2-iodobenzaldehyde, ethyl isobutyrylacetate and concentrated ammonium hydroxide by the procedures described in Example 125, Steps A-B. 1H NMR (300 MHz, CDCl3): δ 0.94 (t, J=7.0 Hz, 6 H), 1.30 (d, J=6.6 Hz, 6 H), 1.34 (d, J=6.6 Hz, 6 H), 3.19 (septet, J=6.6 Hz, 2 H), 4.0 (q, J=7.0 Hz, 4 H), 7.0-7.40 (m, 3 H), 7.85 (m, 1 H).

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: n-Butyl lithium solution (2.5M in hexanes, 0.84 mL, 2.10 mmol) was added to 1-(dimethylaminomethyl)imidazole (prepared by the method detailed in JOC 1988, 53, 5685-5689; 0.25 g, 2.0 mmol) in tetrahydrofuran (8 mL) at ≦−65° C. with stirring under nitrogen. After 1 hour at this temperature a solution of 2-iodobenzaldehyde (0.50 g, 2.09 mmol) in tetrahydrofuran (1 mL) was added and the mixture allowed to return to ambient temperature overnight. Dilute hydrochloric acid (2N, 10 mL) was then added and organic solvent removed in vacuo before neutralising with sodium bicarbonate. Dichloromethane (3×30 mL) extracts were washed with saturated brine then dried (MgSO4), filtered and concentrated in vacuo to give a yellow oil. Purification by flash column chromatography eluting with 50% ethyl acetate/isohexane gave a white solid of 1H-imidazol-2-yl(2-iodophenyl)methanol (0.22 g, 38%). 1H NMR (500 MHz, d6-DMSO) δ 11.94 (1H, s), 7.80 (1H, dd, J=1.0, 7.8 Hz), 7.53 (1H, dd, J=1.7, 7.8 Hz), 7.41-7.37 (1H, m), 7.04-7.00 (2H, m), 6.74 (1H, s), 6.20 (1H, d, J=4.7 Hz), 5.83 (1H, d, J=4.7 Hz); m/z (ES+) 301 [MH+]. prepared by the method organic solvent removed in vacuo Dichloromethane (3×30 mL) extracts were washed with saturated brine then dried (MgSO4) filtered concentrated in vacuo to give a yellow oil Purification by flash column chromatography eluting with 50% ethyl acetate/isohexane

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

実験手順: n-Butyl lithium solution (2.5M in hexanes, 0.84 mL, 2.10 mmol) was added to 1-(dimethylaminomethyl)imidazole (prepared by the method detailed in JOC 1988, 53, 5685-5689; 0.25 g, 2.0 mmol) in tetrahydrofuran (8 mL) at ≦−65° C. with stirring under nitrogen. After 1 hour at this temperature a solution of 2-iodobenzaldehyde (0.50 g, 2.09 mmol) in tetrahydrofuran (1 mL) was added and the mixture allowed to return to ambient temperature overnight. Dilute hydrochloric acid (2N, 10 mL) was then added and organic solvent removed in vacuo before neutralising with sodium bicarbonate. Dichloromethane (3×30 mL) extracts were washed with saturated brine then dried (MgSO4), filtered and concentrated in vacuo to give a yellow oil. Purification by flash column chromatography eluting with 50% ethyl acetate/isohexane gave a white solid of 1H-imidazol-2-yl(2-iodophenyl)methanol (0.22 g, 38%). 1H NMR (500 MHz, d6-DMSO) δ 11.94 (1H, s), 7.80 (1H, dd, J=1.0, 7.8 Hz), 7.53 (1H, dd, J=1.7, 7.8 Hz), 7.41-7.37 (1H, m), 7.04-7.00 (2H, m), 6.74 (1H, s), 6.20 (1H, d, J=4.7 Hz), 5.83 (1H, d, J=4.7 Hz); m/z (ES+) 301 [MH+]. prepared by the method organic solvent removed in vacuo Dichloromethane (3×30 mL) extracts were washed with saturated brine then dried (MgSO4) filtered concentrated in vacuo to give a yellow oil Purification by flash column chromatography eluting with 50% ethyl acetate/isohexane

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

実験手順: In a flask, 2-iodobenzyl alcohol (4 g, 17.09 mmol) was dissolved in dichloromethane (MC, 85 ml), and then, manganese oxide (MnO2, 14.86 g, 170.92 mmol) was added thereto. The obtained reaction product was stirred under the reflux condition. When the reaction was completed, the obtained reaction product was cooled to the room temperature, and then, fiteated and concentrated using celite, to obtain the title compound (3.6 g, yield 91%). The obtained reaction product the obtained reaction product fiteated and concentrated

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

実験手順: The substantially same method as described in Preparation Example 284 was conducted, except that 2-fluorobenzaldehyde (Aldrich No. F4807) was used instead of 2-iodobenzaldehyde (Preparation Example 63) to obtain the title compound (1.82 g, yield 20˜40%). The substantially same method as described in Preparation Example 284

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

実験手順: The substantially same method as described in Preparation Example 284 was conducted, except that 2-fluorobenzaldehyde (Aldrich No. F4807) was used instead of 2-iodobenzaldehyde (Preparation Example 63) to obtain the title compound (1.82 g, yield 20˜40%). The substantially same method as described in Preparation Example 284

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

実験手順: In a flask, 2-iodobenzyl alcohol (4 g, 17.09 mmol) was dissolved in dichloromethane (MC, 85 ml), and then, manganese oxide (MnO2, 14.86 g, 170.92 mmol) was added thereto. The obtained reaction product was stirred under the reflux condition. When the reaction was completed, the obtained reaction product was cooled to the room temperature, and then, fiteated and concentrated using celite, to obtain the title compound (3.6 g, yield 91%). The obtained reaction product the obtained reaction product fiteated and concentrated