1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 86609636, compound

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Reaction Conditions

Reaction Steps

Xylene (200 mL) was added to 7-iodo-5-nitro-1-benzofuran (2.78 g, 9.61 mmol), tert-butyl piperidin-4-ylcarbamate (2.31 g, 12.0 mmol), Pd2(dba)3 (0.22 g, 0.24 mmol), Xantphos (0.56 g, 0.96 mmol) and sodium tert-butoxide (1.29 g, 13.0 mmol). The mixture was heated at 120° C. with stirring for 16 h. The reaction mixture was allowed to reach room temperature, filtered through a pad of Celite, and concentrated in vacuo. The crude product was purified by flash chromatography, using DCM as eluent, to afford 1.03 g (84%) of the title product. HPLC 94%, RT: 2.770 (System B; 10-97% MeCN over 3 min). 1H NMR (270 MHz, methanol-d4) δ ppm 1.45 (s, 9H) 1.62-1.72 (m, 2H) 1.75-2.03 (m, 2H) 2.94-3.02 (m, 2H) 3.55-3.57 (m, 1H) 3.88-3.93 (m, 2H) 7.01 (d, J=2.23 Hz, 1H) 7.64 (d, J=2.23 Hz, 1H) 7.93 (d, J=2.23 Hz, 1H) 8.13 (d, J=2.23 Hz, 1H). LC-MS 362 (M+H)+.

Provenance & Evidence