Application of 153034-90-3, 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. 153034-90-3, name is 2-Chloro-4-iodonicotinaldehyde, molecular formula is C6H3ClINO, 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.
According to GP1, 2-chloro-4-iodonicotinaldehyde (989 mg, 3.70 mmol), CsF (112 mg, 0.74 mmol), and t-BuMe2SiCN (784 mg, 5.60mmol) were dissolved in anhyd MeCN (3.7 mL). The reaction mixture was stirred at 25 C for 12 h. The resulting mixture was diluted with H2O (20 mL) and extracted with EtOAc (3 × 40 mL). The combined organic phases were dried (anhyd MgSO4), filtered, and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography on silica gel (i-hexane/EtOAc, 9:1 + Et3N 2%) yielding 2-(tert-butyldimethylsilyloxy)-2-(2-chloro-4-iodopyridin-3-yl)acetonitrile as a light yellow solid (1.5 g, 98%); mp 83.4-85.2 C.IR (Diamond-ATR, neat): 2955, 2859, 1636, 1548, 1472, 1337, 1302,1255, 1186, 1066, 939, 833, 781 cm-1.1H NMR (400 MHz, CDCl3): delta = 7.99 (d, J = 5.2 Hz, 1 H), 7.85 (d, J = 5.2Hz, 1 H), 6.24 (s, 1 H), 0.94 (s, 9 H), 0.31 (s, 3 H), 0.13 (s, 3 H).13C NMR (101 MHz, CDCl3): delta = 150.3, 149.9, 135.5, 132.5, 116.7,110.3, 65.2, 25.4, 18.0, -4.9, -5.1.MS (70 eV, EI): m/z (%) = 353 (28), 351 (79), 323 (52), 296 (4), 226(35), 224 (100), 209 (12), 150 (6).HRMS (EI): m/z [M – C4H9]+ calcd for C9H9ClIN2OSi: 350.9217; found:350.9210.
According to the analysis of related databases, 153034-90-3, the application of this compound in the production field has become more and more popular.
Reference:
Article; Castello-Mico, Alicia; Knochel, Paul; Synthesis; vol. 50; 1; (2018); p. 155 – 169;,
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