Pyridine → 5-[(2-Adamantan-1-ylmethyl-5-phenyl-1H-pyrrole-3-carbonyl)-amino]-isophthalic Acid Dibenzyl Ester

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Reaction Steps

To a suspension of the product of step c above (290 mg, 0.91 mmol) in DCM (5 ml) was added thionyl chloride (200 μl, 2.74 mmol) and one drop of DMF. The mixture was stirred at room temperature for 30 min, the solvent was evaporated and the residue was coevaporated with DCM (2×5 ml). 5-Amino-isophthalic acid dibenzyl ester (361 mg, 1.00 mmol) was added to the residue followed by anhydrous pyridine (2 ml). The solution was kept at room temperature for 16 h and diluted with DCM (30 ml). The organic phase was washed with 2M hydrochloric acid (2×20 ml), brine (20 ml), dried (MgSO4) and the solvent was evaporated. The residue was purified by flash column chromatography (silica, DCM/hexane/ethyl acetate 9:9:2) to afford the product as pale yellow solid (300 mg, 45%). 1H NMR (300 MHz, CDCl3) 8.48 (3H, s), 8.30 (1H, br s), 7.69 (1H, s), 7.49-7.27 (15H, m), 6.66 (1H, d), 5.40 (4H, s), 2.91 (2H, s), 1.95 (3H, br s), 1.63 (12H, m).

Provenance & Evidence