Cesium carbonate → 2-(4-(1,3-Dioxan-2-yl)-3,5-dimethylphenyl)-5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine

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Reaction Conditions

Reaction Steps

A mixture of 5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (23.2 mg, 92 μmol), 2-(4-bromo-2,6-dimethylphenyl)-1,3-dioxane (25 mg, 92 μmol), PdCl2(AmPhos)2 (4.8 mg, 7.7 μmol), and cesium carbonate (90 mg, 276 μmol) in DMF (1.0 mL) was heated (microwave) at 190° C. under argon for 30 min, then at 200° C. for 30 min. The reaction mixture was then partitioned between EtOAc (40 mL) and water (10 mL). The organic layer was separated and sequentially washed with water (2×10 mL) and brine (10 mL), then dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-70% EtOAc/Hex,) furnished 2-(4-(1,3-dioxan-2-yl)-3,5-dimethylphenyl)-5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine as a yellow solid. MS (ESI) m/z: Calculated: 442.2; Observed: 443.2 (M++1).

Provenance & Evidence