Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 52548-63-7, name is 5-Fluoro-2-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H4FIO2
To a solution of 1H-pyrrolo[2,3-c]pyridine (70 g, 0.59 mol) in MeOH (1,050 mL) and H2O (350 mL) was added KOH (83 g, 1.48 mol) and tert-butyl 3-oxopiperidine-1- carboxylate (259 g, 1.30 mol). The resulting mixture was stirred at 75-80 oC (oil bath temperature) for 18 h. The reaction mixture was concentrated under reduced pressure to remove MeOH, then H2O (700 mL) was added and the mixture was extracted with EtOAc (3 ¡Á 1000 mL). The organic layers were filtered and the filtered cake was washed with EtOAc (2 ¡Á 150 mL) to afford tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4- dihydropyridine-1(2H)-carboxylate (75 g, 42% yield) as white solid. The organic layer was concentrated under reduced pressure to about 250 mL. The residue was stirred at 5-9 oC for 18 h. The residue was filtered and the filtered cake was washed with EtOAc (2 ¡Á 60 mL) to give a mixture of tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,6- dihydropyridine-1(2H)-carboxylate and tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4- dihydropyridine-1(2H)-carboxylate (1:3.5 via LCMS; (28 g, 16% yield) as white solid. tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4-dihydropyridine-1(2H)- carboxylate: Yield: 75 g (42%); Rt value: 0.570 (LCMS Method C); (M+H)+ = 300.1; 1H NMR (MeOD, 400 MHz): delta ppm 8.65-8.70 (d, J = 2.8 Hz, 1H), 8.05-8.15 (d, J = 5.6 Hz, 1H), 7.70-7.90 (m, 1H), 7.54 (s, 1H), 7.35-7.50 (m, 1H), 3.60-3.75 (m, 2H), 2.50-2.60 (t, J = 5.6 Hz, 2H), 2.00-2.10 (m,2H), 1.55-1.60 (m, 9H). Mixture of tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,6-dihydropyridine- 1(2H)-carboxylate and tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4-dihydropyridine- 1(2H)-carboxylate: Rt value: 0.568 (LCMS Method C); (M+H)+ = 300.1. A suspension of tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4-dihydropyridine- 1(2H)-carboxylate and tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,6-dihydropyridine- 1(2H)-carboxylate (1 g, 3.34 mmol, ~10:1 ratio of isomers), 5-fluoro-2-iodobenzoic acid (977 mg, 3.67 mmol), K2CO3 (1.15 g, 8.33 mmol), CuI (63 mg, 0.334 mmol) and 1,10- phenanthroline (60 mg, 0.334 mmol) in DMF (13 mL, 0.26 M reaction concentration) was degassed with N2 for 15 min. The reaction mixture was then placed under N2 and heated to 70 oC for 24 h. The reaction was then cooled to room temperature and filtered through a plug of Celite using a small amount of DMF to rinse the filter cake. The DMF solution was cooled to 0 oC and a 1N aq. HCl solution (~10 mL) was added, maintaining a pH of ~5, followed by the addition of H2O (~10 mL) and EtOAc for the extraction. The EtOAc layer was separated and the aqueous layer (pH~5) was extracted three additional times with EtOAc. The EtOAc layers were combined and washed with H2O followed by brine. After drying over Na2SO4, the EtOAc layer was evaporated and the resulting residue was dried under high vacuum overnight to afford ~2 grams of crude 2-(3-(1-(tert-butoxycarbonyl)-1,4,5,6-tetrahydropyridin-3-yl)-1H-pyrrolo[2,3-c]pyridin- 1-yl)-5-fluorobenzoic acid and 2-(3-(1-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridin-3- yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)-5-fluorobenzoic acid (>10:1 ratio of isomers). The crude material was used directly for the next step without further purification. LCMS: 5.748 min (LCMS Method G): 438.47 (M + 1).1H NMR (400 MHz, CDCl3): delta 8.52-8.48 (m, 1H), 8.20-8.15 (m, 1H), 8.07 (bs, 1H), 8.01 (s, 1H), 7.85 (d, 1H, J = 8.4 Hz), 7.76 (s, 1H), 7.55 (bs, 1H), 7.42 (d, 1H, J = 5.2 Hz), 3.67 (bs, 2H), 2.50-2.47 (m, 2H), 2.06-2.01 (m, 2H), 1.54 (s, 9H).
According to the analysis of related databases, 52548-63-7, the application of this compound in the production field has become more and more popular.
Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David A.; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen D.; SINGH, Suresh B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; (285 pag.)WO2018/53267; (2018); A1;,
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