Sodium Carbonate → HCID 53469824, compound

Participants

Reaction Conditions

Reaction Steps

To a 25 mL pressure tube was charged 7-iodo-3-[1-(phenylacetyl)-2,3-dihydro-1H-indol-5-yl]thieno[3,2-c]pyridin-4-amine (182 mg, 0.356 mmol), 3-pyridinylboronic acid (43.7 mg, 0.356 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (14.53 mg, 0.018 mmol), and sodium carbonate (75 mg, 0.712 mmol) followed by dioxane (5 mL), and water (1 mL). The reaction was heated at 120° C. for 30 min in microwave reactor. Water (20 mL) and ethyl acetate (20 mL) were added and the layers were separated. The organic layer was washed with brine, concentrated, and the residue purified by silica gel chromatography (0%-100% EtOAc in hexanes) to afford the tittle compound 3-[1-(phenylacetyl)-2,3-dihydro-1H-indol-5-yl]-7-(3-pyridinyl)thieno[3,2-c]pyridin-4-amine (85 mg) as a gray solid. LC-MS (ES) m/z=463.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.88 (d, J=1.8 Hz, 1H) 8.62 (dd, J=4.8, 1.5 Hz, 1H) 8.18 (d, J=8.1 Hz, 1H) 8.10 (dt, J=8.1, 1.9 Hz, 1H) 7.96 (s, 1H) 7.56 (dd, J=8.1, 4.8 Hz, 1H) 7.50 (s, 1H) 7.23-7.40 (m, 7H) 5.63 (br. s., 2H) 4.26 (t, J=8.5 Hz, 2H) 3.90 (s, 2H) 3.24 (t, 2H)

Provenance & Evidence