Category: 95652-80-5

Reference of 95652-80-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 95652-80-5 as follows.

To a stirred solution of 31(6.83 g, 30.7 mmol) in THF (120 mL) was added i-PrMgCl·LiCl (ca.1.0 Msolution in THF, 32.2 mL, 32.2 mmol) at -20C. After 2 h, DMF (7.2 mL, 92.1 mmol) was added dropwise at -20C. The resulting mixture was stirred at room temperature for 30 min. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material including 12was applied to the following reaction without further purification.To a suspension of the crude material including 12and NaOAc (3.78 g, 46.1 mmol) in the 1 : 1 mixture of n-BuOH and toluene (total 120 mL) was added Pd(dppf) Cl2 (1.12 g, 1.54 mmol) at room temperature. The resulting mixture was stirred under ordinary CO pressure (balloon) at 100C for 18 h. The reaction was quenched with saturated aqueous NH4Cl, filtered through a pad of Celite and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, n-hexane-EtOAc=2 : 1) to afford 13(4.75 g, 65% 2 steps) as a yellow oil.13: IR (film, cm-1): 2963, 2876, 1721, 1692, 1595, 1481, 1337, 1277, 1261, 1219, 1138, 1072, 1022; 1H-NMR (CDCl3, 500 MHz) delta: 10.39 (s, 1H), 8.18 (d, J=8.50 Hz, 1H), 6.94 (d, J=8.50 Hz, 1H), 4.44 (t, J=6.80 Hz, 2H), 4.06 (s, 3H), 1.83-1.76 (m, 2H), 1.54-1.45 (m, 2H), 0.99 (t, J=7.37 Hz, 3H); 13C-NMR (CDCl3, 125 MHz) delta: 189.1, 166.1, 165.2, 150.7, 138.6, 125.9, 114.1, 66.3, 54.5, 30.5, 19.2, 13.7; HR-MS (ESITOF): Calcd for C12H15NO4Na [(M+Na)+] 260.0893. Found 260.0891.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,95652-80-5, its application will become more common.

Reference:
Article; Inai, Makoto; Ouchi, Hitoshi; Asahina, Aya; Asakawa, Tomohiro; Hamashima, Yoshitaka; Kan, Toshiyuki; Chemical and Pharmaceutical Bulletin; vol. 64; 7; (2016); p. 723 – 732;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 95652-80-5, name is 2-Chloro-6-methoxynicotinaldehyde, molecular formula is C7H6ClNO2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. name: 2-Chloro-6-methoxynicotinaldehyde

Palladium (II) acetate (0.08 g, 0.36 mmol) , caesium carbonate (2.23 g, 6.83 mmol), 2-di-tert-butylphosphino-2 ‘ , 4 ‘ , 6 ‘ – triisopropylbiphenyl (t-Butyl XPhos) (0.290 g, 0.68 mmol), compound 6 (0.59 g, 3.41 mmol), and 4 (0.88 g, 4.44 mmol) and toluene (30 mL) were combined and purged by a stream of argon for 3 minutes. The reaction was sealed and heated at 80 C for 4h. The mixture was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure. The product was purified by flash chromatography on silica gel using 0-60% ethyl acetate in hexane. The product was recrystallized from diethyl ether (488 mg, 35%). mp : 132.0-133.0 C; 1H NMR (600MHz, CDC13) delta [ppm] : 10.22 (d, J=0.8 Hz, 1H) , 8.06 (d, J=8.4 Hz, 1H) , 7.44-7.41 (m, 3H) , 7.37-7.34 (m, 1H) , 7.32-7.30 (m, 2H) , 7.28 (d, J=7.5 Hz, 1H) , 7.26 (m, 1H) , 6.45 (dd, Jl=8.4 Hz, J2=0.8 Hz, 1H) , 5.52 (s, 2H) , 4.08 (3H), 2.28 (s, 3H) ; 13C NMR (151 MHz, DMSO-d6) delta [ppm] : 187.8, 166.6, 165.2, 143.2, 142.0, 140.5, 135.0, 134.8, 130.5, 129.5, 128.7, 128.3, 127.1, 125.7, 112.5, 103.9, 67.8, 54.1, 16.5; IR V (ATR cm-1): 3063, 2961, 2870, 1671, 1591, 1460, 1330, 1277; HRMS (ESI-TOF) Calcd for C21H19N03Na [M+Na]+ : 356.1263; found [M+Na]+: 356.1256.

With the rapid development of chemical substances, we look forward to future research findings about 95652-80-5.

Reference:
Patent; RIJKSUNIVERSITEIT GRONINGEN; DOeMLING, Alexander; (85 pag.)WO2017/118762; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem