Cesium carbonate → HCID 49838784, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave vial equipped with magnetic stir bar, 50 mg (0.14 mmol) of 6-bromo-2-[trans-3-(1-piperidinyl)cyclobutyl]benzothiazole (prepared as described in Cowart, et al. Benzothiazole cyclobutylamine derivatives, US Patent Publication No. 2007/0066588(A1)) was added, followed by (S)-3-hydroxypyrrolidin-2-one (50 mg, 0.50 mmol), Pd2(dba)3 (4.0 mg, 0.0044 mmol), xantphos (6.9 mg, 0.012 mmol) and Cs2CO3 (68 mg, 0.21 mmol). The reaction vial was sealed with an aluminum cap, and purged with N2, then dioxane (2 mL) was introduced via a syringe. The reaction mixture was then heated in a microwave oven at 150° C. for 60 minutes. The reaction mixture was cooled to room temperature, filtered, and the solvent was removed under vacuum, after which the residue was purified via chromatography on silica gel, eluting with a gradient of 0-10% methanol in dichloromethane, to give the desired product (21 mg, 40%). 1H NMR (300 MHz) δ 8.34 (d, J=2.2, 1H), 7.97 (d, J=8.9, 1H), 7.61 (dd, J=2.2, 8.9, 1H), 4.51 (dd, J=8.2, 9.7, 1H), 3.86 (m, 3H), 3.13 (m, 1H), 2.66 (m, 1H), 2.58 (m, 4H), 2.32 (m, 3H), 2.15 (ddd, J=9.5, 12.6, 19.1, 1H), 1.61 (m, 6H), 1.48 (m, 2H). MS (ESI) m/z=372.0 (M+H)+

Provenance & Evidence