Methanol → HCID 53469634, 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), 1-Boc-pyrazol-4-boronic acid pinacol ester (88 mg, 0.299 mmol), and PdCl2(dppf)-CH2Cl2 adduct (9 mg, 0.011 mmol) in 1,4-Dioxane (2.0 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 de-Boc 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, 50%-100% EtOAc in hexanes gradient over 15 minutes, then EtOAc for 5 minutes, then 0-10% MeOH in EtOAc over 20 minutes) to give 3-[1-(phenylacetyl)-2,3-dihydro-1H-indol-5-yl]-7-(1H-pyrazol-4-yl)thieno[3,2-c]pyridin-4-amine (50 mg, 0.105 mmol, 53.3% yield) as a light gray solid. LC/MS (ES) m/z=452 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 3.24 (t, J=8.34 Hz, 2H), 3.89 (s, 2H), 4.26 (t, J=8.46 Hz, 2H), 5.40 (br. s., 2H), 7.22-7.30 (m, 2H), 7.30-7.40 (m, 5H), 7.48 (s, 1H), 7.95 (br. s., 1H), 8.06 (s, 1H), 8.12-8.21 (m, 2H), 13.10 (br. s., 1H).

Provenance & Evidence