Related Products of 175205-81-9 , The common heterocyclic compound, 175205-81-9, name is 2-Bromo-4-(trifluoromethyl)pyridine, molecular formula is C6H3BrF3N, 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.
2-Bromo-4-(trifl”uoromethyl)pyridine (171 mu, 1.382 mmol) in dry tetrahydrofuran (1 mL) was added to butyllithiuni (2.5 M in Hexanes) (885 mu, 1 .416 mmol) in dry tetrahydrofuran (2 mL) at -78 °C. The reaction mixture was stirred at -78 °C for 45 minutes, then a solution of (R)-methyl 6-(( I -ethyl- 1 H-pyrazol~4~yl)sulfonyl)- 1 -(4-fluorophenyl)-4,4a,5,6,7,8-hexahydro- 1 H-pyrazolo[3,4-g]isoquinoline-4a-carboxylate ( 220 mg, 0.453 mmol) in dry tetrahydrofuran (2 mL) was added dropwise and the reaction mixture stirred for 1 hour at -78 °C. Water ( 10 mL) was added and the reaction mixture was stirred at room temperature for 10 minutes. The aqueous phase was extracted with ethyl acetate (2 x 15 mL), and the combined organic layers were washed with brine (20 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to give an orange oil. The crude product was purified by chromatography on silica gel (gradient: 0- 80percent ethyl acetate in isohexane) and preparative HPLC (Waters, Acidic (0.1percent Formic acid), Waters X-Select Prep-C18, 5 muetaiota, 19×50 mm column, 35-70percent acetonitrile in water) to afford (R)-(6-(( 1 -ethyl- 1 H-pyrazol-4-yl)sulfonyl)- 1 -(4-fluorophenyl)-4,4a,5,6,7,8-hexahydro- 1 H- pyrazolo 3,4-g]isoquinolin-4a-yr)(4-(tofluoromemyl)pyridin-2-yl)methanone (23 mg) as a white solid. LCMS (Method F, ES-API): RT 3.00 min, m FontWeight=”Bold” FontSize=”10″ I = 601 .2; 1 1 1 NMR (400 MHz, CDC13): delta 8.88-8.87 Omicron Pi. m), 8.15 (1H, m), 7.71-7.69 (2H, m), 7.67 (IH, d. j = 0.6 Hz), 7.47-7.42 (2H, m), 7.30 (IH, s), 7.20-7.14 (2H, m), 6.51 (1H, d, J = 2.0 Hz), 5.44 (IH, dd, J = 12.0, 2.0 Hz), 4.22- 4.16 (3H, m), 3.80-3.76 (IH, m), 2.94 (IH, d, J = 16.9 Hz), 2.88-2.79 (IH, m), 2.67 (IH, d, J = 12.3 Hz), 2.52-2.40 (2H, m), 1.51 (3H, t, j = 7.3 Hz).
The synthetic route of 175205-81-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; CORCEPT THERAPEUTICS, INC.; HUNT, Hazel; JOHNSON, Tony; RAY, Nicholas; WALTERS, Iain; WO2013/177559; (2013); A2;,
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