Some common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, molecular formula is C10H7FO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: Methyl 3-(4-fluorophenyl)propiolate
To a solution ofN-(4-(benzyloxy)pyridin-3-yl)methanesulfonamide (9.0 g, 30.0mmol) in DCM (100 mL) was added (0-(mesitylsulfonyl)hydroxylamine) (20 g, 92 mmol) inDCM (20 mL) dropwise quickly at 0C under N2, and stirred for 2 hat room temperature. Afterconcentrated and the residue was dissolved in MeOH, and re-concentrated again. The residuewas dissolved in DMF (20 mL), and then added slowly dropwise to a mixture ofmethyl3-(4-15 fluorophenyl)propiolate (6 g, 34 mmol) and K2C03 (21 g, 154 mmol) in DMF (100 mL) at 0Cunder N2 . The mixture was stirred overnight at room temperature. The reaction mixture wasthen concentrated in vacuo and the resulting residue was suspended in H20 and extracted withDCM. The organic layer was washed with H20, brine and concentrated in vacuo. The residueobtained was purified using flash column chromatography on silica gel (eluted with PE I EtOAc20 from 5 I 1 to 3 I 1) to give methyl 5-(benzyloxy)-2-( 4-fluorophenyl)-6-(Nmethylmethylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxylate (3.5 g, yield: 24%). 1H-NMR(CDCh, 400 MHz) 8 8.54 (s, 1H), 7.70~7.74 (m, 2H), 7.68 (s, 1H), 7.42~7.44 (m, 5H), 7.13 (t, J= 8.8 Hz, 2H), 5.24 (s, 2H), 3.80 (s, 3H), 3.29 (s, 3H), 2.81 (s, 3H). MS (M+Ht: 484.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 42122-44-1, its application will become more common.
Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; BROCKUNIER, Linda L.; NARGUND, Ravi; MARCANTONIO, Karen; ZORN, Nicolas; XIAO, Dong; PENG, Xuanjia; LI, Peng; GUO, Tao; WO2014/121416; (2014); A1;,
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