Cesium carbonate → HCID 67175880, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2′-amino-1′-benzyl-6-bromo-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (17.3 mg, 0.04 mmol) in 1,4-dioxane (1.5 mL) was added Cs2CO3 (excess), 3-cyanophenylboronic acid (excess), and catalytical amount of PdCl2dppf. After degassing, the resulting mixture was heated in a CEM microwave reactor at 130° C. for 30 min. Solvent was removed in vacuo and the residue was purified by reverse phase HPLC to give 3-((2R,4R)-2′-amino-1′-benzyl-5′-oxo-2-phenyl-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)benzonitrile (6.0 mg, 33%) as a TFA salt (25b) and 3-((2S,4R)-2′-amino-1′-benzyl-5′-oxo-2-phenyl-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)benzonitrile (0.86 mg, 4.8%) as a TFA salt. (25a). 1H NMR (400 MHz, CD3OD): 7.84-7.60 (m, 4 H), 7.74-7.24 (m, 12 H), 7.12 (d, 1 H), 5.92 (d, 1 H), 4.62 (s, 2 H), 2.60 (d, 1 H), 2.42 (d, 1 H); MS m/z 485 (M+H+) (25b). 1H NMR (400 MHz, CD3OD): 7.74-7.36 (m, 16 H), 7.16 (d, 1 H), 5.24 (d, 1 H), 5.08, 5.00 (two d, 2 H), 2.64 (d, 1 H), 2.56 (d, 1 H); MS m/z 485 (M+H+) (25a).

Provenance & Evidence