Cesium fluoride → HCID 55283822, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-iodo-1,3-dihydro-2-benzofuran-5-amine (563 g, 2.16 mmol) in 1,4-dioxane (15 mL) under N2 was added CsF (1.15 g, 7.56 mmol), MeB(OH)2 (387 g, 6.47 mmol) and PdCl2(DPPF) (176 mg, 0.216 mmol). The mixture was heated at 80° C. for 4 h. The mixture was cooled to room temperature and then diluted with EtOAc (40 mL) and water (40 mL). The mixture was filtered through Celite. The organic layer was separated and the aqueous layer was extracted with EtOAc (2×15 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to afford 4-methyl-1,3-dihydro-2-benzofuran-5-amine. LCMS calc.=150.1; found=149.9 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 6.92 (d, J=7.8 Hz, 1H); 6.66 (d, J=7.9 Hz, 1H); 5.11 (s, 4H); 3.63 (br s, 2H); 2.08 (s, 3H)

Provenance & Evidence