Potassium Carbonate → HCID 89717937, compound

Participants

Reaction Conditions

Reaction Steps

In a 2-5 mL microwave vial was added methyl 2-benzyl-4-chloro-9H-pyrimido[4,5-b]indole-7-carboxylate (0.100 g, 0.284 mmol), (E)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)piperidine (0.113 g, 0.426 mmol), potassium carbonate (0.106 g, 0.768 mmol) and Pd(Ph3P)4 (0.05 g, 0.044 mmol). The vial was purged with N2 (3 vacuum+refill cycles). DME (2.84 mL) and water (0.398 mL) were added and the vial was flushed with N2 (one vacuum+refill) and then heated to 110° C. while stirred for 24 hours. After cooling, the mixture was concentrated to dryness under reduced pressure and the residue was purified by flash chromatography to give (E)-methyl 2-benzyl-4-(4-(piperidin-1-yl)but-1-en-1-yl)-9H-pyrimido[4,5-b]indole-7-carboxylate (55 mg, 0.121 mmol, 42.6% yield) as a light yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.41 (s, 2H) 1.50-1.61 (m, 4H) 2.30-2.47 (m, 4H) 2.53-2.59 (m, 2H) 2.59-2.70 (m, 2H) 3.91 (s, 3H) 4.27 (s, 2H) 7.16-7.24 (m, 1H) 7.29 (t, J=7.6 Hz, 2H) 7.34-7.43 (m, 4H) 7.88 (dd, J=8.2, 1.4 Hz, 1H) 8.07 (d, J=1.4 Hz, 1H) 8.41 (d, J=8.2 Hz, 1H) 12.48 (s, 1H); HRMS m/z 455.2442 (M+H)+; HPLC 100% @ 220 nm and 99.4% @ 254 nm, RT=1.84 minutes.

Provenance & Evidence