Adding a certain compound to certain chemical reactions, such as: 363-51-9, name is 2-Chloro-6-fluoroaniline, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 363-51-9, Product Details of 363-51-9
To 2-chloro-6-fluoroaniline (0.183 g, 1.259 mmol) and 2-(2-chloroquinolin-8-yl)- 6,7-dihydro-lH-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1 ; 0.075 g, 0.252 mmol) was added LHMDS (1.0 M solution in THF ; 1.259 ml, 1.259 mmol). The reaction was sealed and stirred 1 h at RT, then for 3h at 70 C. The reaction was subsequently cooled to RT and stirred overnight. 1.5 mL DMSO and 10 drops TFA were added. The mixture was filtered and purified by rpHPLC (Phenomenex Gemini 150 x 30 mm Cis column, 10-80 % ACN/H20 with 0.1 % TFA). The product-containing fractions were concentrated in vacuo, and the residue was partitioned between saturated aq. NaHCC and DCM. The aq. layer was extracted with DCM (3x), and the combined organic extracts were dried over anhydrous Na2S04, filtered, and concentrated in vacuo. The material was dissolved in DCM/MeOH, adsorbed onto 0.75 g silica gel, and purified by silica gel chromatography using 0-50% 90/10 MeOH/DCM in DCM. The product-containing fractions were concentrated to separately afford 2-(2-((2-chloro-6-fluorophenyl)amino)quinolin-8-yl)- 6,7-dihydro-lH-pyrrolo[3,2-c]pyridin-4(5H)-one (0.022 g, 0.054 mmol, 21 % yield) as a light-yellow solid and 2-(2-((2-chloro-6-fluorophenyl)amino)quinolin-8-yl)-lH- pyrrolo[3,2-c]pyridin-4(5H)-one (0.0037 g, 9.14 muetaiotaomicron, 4%> yield) as a yellow solid. 2-(2- ((2-Chloro-6-fluorophenyl)amino)quinolin-8-yl)-6,7-dihydro-lH-pyrrolo[3,2-c]pyridin- 4(5H)-one (7): H NMR (400 MHz, DMSO-d6) delta ppm 11.82 (1 H, br. s), 9.34 (1 H, s), 8.16 (1 H, d, J=9.0 Hz), 8.01 (1 H, dd, J=7.6, 1.6 Hz), 7.55 – 7.67 (2 H, m), 7.41 – 7.54 (2 H, m), 7.28 (1 H, t, J=7.7 Hz), 7.13 (1 H, d, J=9.0 Hz), 6.83 – 6.98 (2 H, m), 3.32 – 3.44 (2 H, m), 2.43 (2 H, t, J=6.8 Hz), m/z (ESI, +ve) 406.9 (M+H)+. 2-(2-((2-Chloro-6- fluorophenyl)amino)quinolin-8-yl)-lH-pyrrolo[3,2-c]pyridin-4(5H)-one (12): H NMR (400 MHz, DMSO-de) delta ppm 12.09 (1 H, br. s), 10.68 (1 H, d, J=6.1 Hz), 9.41 (1 H, s), 8.1 1 – 8.26 (2 H, m), 7.43 – 7.76 (4 H, m), 7.34 (1 H, t, J=7.7 Hz), 7.18 – 7.25 (1 H, m), 7.14 (1 H, d, J=9.0 Hz), 6.86 – 7.00 (1 H, m), 5.91 (1 H, d, J=6.8 Hz). m/z (ESI, +ve) 405.2 (M+H)+.
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Reference:
Patent; AMGEN INC.; CEE, Victor; CHAVEZ, JR., Frank; CHEN, Jian J.; HARRINGTON, Essa Hu; HERBERICH, Bradley; JACKSON, Claire L. M.; LANMAN, Brian A.; NGUYEN, Thomas T.; NORMAN, Mark H.; PETTUS, Liping H.; REED, Anthony B.; SMITH, Adrian L.; TAMAYO, Nuria A.; TASKER, Andrew; WANG, Hui-Ling; WU, Bin; WURZ, Ryan; WO2013/130660; (2013); A1;,
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