Hydrochloric Acid → HCID 71090134, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,3-dimethyl-1H-isobenzofuran-5-ol (Intermediate 18, 30 mg, 0.18 mmol) and 2-chloro-5-nitro-pyridine (27.5 mg, 0.1736 mmol) in DMF (1 mL) dipotassium carbonate (37.8 mg, 0.2741 mmol) was added and the reaction mixture was stirred for 1.5 hours at 80° C. After cooling the reaction was quenched with water (1 ml), diluted with brine (5 ml) and extracted with ethyl acetate (2×10 ml). The organic layer was dried (Na2SO4), filtered and evaporated and the residue was dissolved in ethanol (3 mL)/water (1 mL). Iron (61.2 mg, 1.1 mmol) and an aqueous 6M solution of hydrogen chloride (0.03 ml, 0.18 mmol) were added and the reaction mixture was stirred for 4 hours at 50° C. The catalyst was filtered off and the resulting solution was diluted with a saturated solution of NaHCO3 (15 ml) and extracted with ethyl acetate (2×20 ml). The organic layer was dried (Na2SO4), filtered and evaporated and the residue was purified by flash chromatography (Biotage system) on silica gel using a SNAP 10 g as column and cyclohexane/ethyl acetate from 80:20 to 30:70 as eluent affording the title compound (20 mg) as colourless oil.

Provenance & Evidence