2-fluoro-4-(2-oxoethyl)benzonitrile

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

実験手順: To a solution of crude 2-fluoro-4-(2-oxoethyl)benzonitrile (900 mg, 5.5 mmol) in 20 mL of DCM was added N-Boc Piperazine (1.0 g, 5.5 mmol) and NaBH(OAc)3 (4.7 g, 22 mmol), the mixture was stirred at room temperature overnight. The reaction was diluted with DCM, and washed with brine, the organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by preparative TLC to give tert-butyl 4-[2-(4-cyano-3-fluorophenyl)ethyl]piperazine-1-carboxylate. washed with brine the organic layer was dried over anhydrous Na2SO4 concentrated The residue was purified by preparative TLC

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-allyl-2-fluorobenzonitrile (1 g, 6.2 mmol) in 1:1 CH2Cl2/MeOH (40 mL) containing pyridine (1 mL, 12.4 mmol) was cooled to −78° C., and O3 was passed through until a blue color was present. N2 was then bubbled through to discharge the blue color and Me2S (5 ml) was added. The reaction mixture was allowed to warm and left overnight. The mixture was washed with 1 N HCl and aqueous NaHCO3 and then dried and concentrated to give crude 2-fluoro-4-(2-oxoethyl)benzonitrile. The material was carried on as the crude. N2 was then bubbled through was added to warm The mixture was washed with 1 N HCl and aqueous NaHCO3 dried concentrated

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

実験手順: A solution of 2-fluoro-4-(2-oxoethyl)benzonitrile (140 mg, 0.88 mmol), 1-[2-(4-nitrophenyl)ethyl]piperazine (170 mg, 0.73 mmol) and NaBH(OAc)3 (620 mg, 2.9 mmol) in anhydrous DCM (10 mL) was stirred at ambient temperature overnight. The reaction was completed according to TLC. The reaction mixture was added 20 mL of DCM, washed with brine, separated the organic layer, dried over anhydrous sodium sulfate and concentrated. The residue was purified by preparative TLC to give the product. 1H-NMR (400 MHz, CDCl3) δ ppm 8.13˜8.16 (d, J=8.6 Hz, 2H), 7.52˜7.55 (t, J=6.6 Hz, 1H), 7.36˜7.38 (d, J=8.6 Hz, 2H), 7.08˜7.12 (m, 2H), 2.89˜3.00 (m, 4H), 2.56˜2.78 (m, 12H). MS m/z: 383 (M+1)+. (0.24 μM) washed with brine separated the organic layer dried over anhydrous sodium sulfate concentrated The residue was purified by preparative TLC to give the product

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-(2,3-dihydroxypropyl)-2-fluorobenzonitrile (500 mg, 2.6 mmol) in 10 mL of methanol and 3 mL of water was cooled to 0° C. by ice bath, then NaIO4 (820 mg, 3.8 mmol) was added and the mixture was stirred at 0° C. for two hours. The reaction was monitored according to TLC. The mixture was filtered and concentrated. The residue was dissolved in DCM, dried over anhydrous sodium sulfate, and then purified by flash column chromatography to give 2-fluoro-4-(2-oxoethyl)benzonitrile. MS m/z: 164 (M+1)+. The mixture was filtered concentrated The residue was dissolved in DCM dried over anhydrous sodium sulfate purified by flash column chromatography