Related Products of 42122-44-1, A common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, molecular formula is C10H7FO2, its 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.
To a cooled solution (0 C, ice bath) containing 3-(3-(N-(2-(tert- butyldimethylsilyloxy)ethyl)methylsulfonamido)pyridin-4-yl)-N-(2-phenylpropan-2- yl)benzamide (0.090 g, 0.12 mmol) and dichloromethane (2 mL) was added O- (mesitylsulfonyl)hydroxylamine (0.080 g, 0.37 mmol) in dichloromethane (2 mL) quickly, dropwise. The solution was maintained at 0 C for 15 min, removed from the cooling bath and maintained at ambient temperature for 2 h. The solution was concentrated, dissolved in methanol (5 mL) and re-concentrated to afford l-amino-3- ( -(2-hydroxyethyl)methylsulfonamido)-4-(3-(2-phenylpropan-2- ylcarbamoyl)phenyl) pyridinium 2,4,6-trimethylbenzenesulfonate as a light yellow foam (470, MH+). The product thus obtained was dissolved in DMF (2.4 mL) and added slowly dropwise over 20 min to a cooled mixture (0C, ice bath) containing potassium carbonate (0.070 g, 0.50 mmol), methyl 3-(4-fluorophenyl)propiolate (0.030 g, 0.19 mmol) and DMF (2.0 mL). The mixture was kept in the cooling bath with stirring and allowed to proceed for 15 h at ambient temperature. The mixture was filtered and concentrated. Purification on silica gel (0-100% ethylacetate/hexanes, 60 min gradient) afforded methyl 2-(4-fluorophenyl)-6-( -(2- hydroxyethyl)methylsulfonamido)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl) pyrazolo[l,5-a]pyridine-3-carboxylate as a yellow residue. 1H NMR (500 MHz,CHLOROFORM-D) delta ppm 8.72 (s, 1 H), 8.24 (s, 1 H), 8.16 (s, 1 H), 7.97 – 8.00 (m, 1 H), 7.89 (t, J=7.93 Hz, 1 H), 7.77 – 7.84 (m, 2 H), 7.50 – 7.59 (m, 2 H), 7.40 – 7.49 (m, 3 H), 7.23 – 7.33 (m, 3 H), 7.12 – 7.19 (m, 3 H), 3.83 (s, 3 H), 3.62 – 3.71 (m, 1 H), 3.39 – 3.46 (m, 1 H), 3.30 – 3.39 (m, 1 H), 3.18 – 3.23 (m, 3 H), 2.63 – 2.72 (m, 1 H), 1.78 (t, J=12.21 Hz, 6 H). LCMS: retention time: 2.403 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters- Sunfire, 5u, CI 8, 4.6 x 50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3CN / 90% H20 / 10 mM TFA and solvent B was 10% H20 / 90% CH3CN / 10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode, m/z 645 (MH+).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PRACITTO, Richard; KADOW, John, F.; BENDER, John, A.; BENO, Brett, R.; GRANT-YOUNG, Katharine; HAN, Ying; HEWAWASAM, Piyasena; NICKEL, Andrew; PARCELLA, Kyle, E.; YEUNG, Kap-Sun; CHUPAK, Louis, S.; WO2011/112186; (2011); A1;,
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