Methanol → HCID 53467819, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-iodo-3-[1-(phenylacetyl)-2,3-dihydro-1H-indol-5-yl]thieno[3,2-c]pyridin-4-amine (101 mg, 0.198 mmol), pyridine-4-boronic acid, pinacol ester (53 mg, 0.258 mmol), and PdCl2(dppf)-CH2Cl2 adduct (8 mg, 9.80 μmol) in 1,4-Dioxane (1.5 mL) and saturated aqueous sodium bicarbonate (0.6 mL, 0.600 mmol) was degassed with Nitrogen for 10 minutes in a microwave vial. The vial was then capped and the mixture was stirred at 120° C. in the microwave for 30 min. LCMS showed complete conversion to the desired product, along with a small de-iodo by-product. The mixture was cooled, poured into water (15 mL), and extracted with ethyl acetate (2×15 mL). The extracts were washed with brine (1×15 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (Analogix, 24 g SiO2, 25%-100% EtOAc in hexanes gradient over 30 minutes, then EtOAc for 10 minutes, then 0-10% MeOH in EtOAc over 20 minutes) to give 3-[1-(phenylacetyl)-2,3-dihydro-1H-indol-5-yl]-7-(4-pyridinyl)thieno[3,2-c]pyridin-4-amine (66 mg, 0.136 mmol, 68.6% yield) as a beige solid. LC/MS (ES) m/z=463 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 3.24 (t, J=8.46 Hz, 2H), 3.90 (s, 2H), 4.26 (t, J=8.46 Hz, 2H), 5.74 (br. s., 2H), 7.23-7.39 (m, 7H), 7.52 (s, 1H), 7.70-7.75 (m, 2H), 8.09 (s, 1H), 8.18 (d, J=8.34 Hz, 0H), 8.65-8.72 (m, 2H).

Provenance & Evidence