Potassium Phosphate, Tribasic → (S)-2-(2-methyl-3-((1,1,1-trifluoropropan-2-yl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Participants

Reaction Conditions

Reaction Steps

Prepared similarly to that described in Example 254 using 2-(3-chloro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 254c; 34 mg, 0.109 mmol), (S)-1,1,1-trifluoropropan-2-amine hydrochloride (32.5 mg, 0.217 mmol, SynQuest Laboratories, Alachua, Fla.), Pd(tBu3P)2 (Strem, Newburyport, Mass.; 5.56 mg, 10.87 μmol), and K3PO4 (92 mg, 0.435 mmol), heating at 100° C. for 2 h. Purification by silica gel (100% DCM to 4% 2 M NH3 in MeOH/DCM) then by rpHPLC (Phenomenex Gemini C18, 10 pan, 150×30 mm; 10-100% ACN/water with 0.1% TFA) provided (S)-2-(2-methyl-3-((1,1,1-trifluoropropan-2-yl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (16% yield). MS (ESI, pos. ion) m/z: 390.2 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 1.61 (d, J=6.85 Hz, 3H) 2.66 (s, 3H) 2.96 (t, J=6.85 Hz, 2H) 3.66 (td, J=6.85, 2.54 Hz, 2H) 4.85 (s, 1H) 4.86-4.96 (m, 1H) 5.35 (br. s., 1H) 7.12 (d, J=2.35 Hz, 1H) 7.47 (t, J=7.82 Hz, 1H) 7.73 (dd, J=8.12, 1.27 Hz, 1H) 7.94 (dd, J=7.63, 1.17 Hz, 1H) 11.60 (br. s., 1H). 19F NMR (376 MHz, DMSO-d6) δ ppm −76.30 (3F, s).

Provenance & Evidence