Pyridine → HCID 66931693, compound

Participants

Reaction Steps

A solution of 4-nitrophenyl chloroformate (0.8 g, 4 mmol) in CH2Cl2 was added to a Wang resin (1 mmol) in CH2Cl2 (9 mL) and pyridine (3 mL). After shaking for 12 h, the resin was washed with 10% dimethylformamide (DMF) in CH2Cl2. A solution of 2,2′-(ethylenedioxy)bisethylenediamine (1.5 g, 10 mmol) and diisopropylethylamine (0.6 g, 5 mmol) in DMF was added to the resin. After shaking for 12 h, the resin was washed with DMF. The resin (7 μmol), 2-fluorenecarboxaldehyde (13 mg, 0.07 mmol), ammonium acetate (22 mg, 0.28 mmol) and 4,4′-difluorobenzil (17 mg, 0.07 mmol) was placed in a reaction vial and suspended in acetic acid (300 μL). The reaction vial was placed in a heat block on a shaker at 100□. The reaction vial was shaken for 5 h. The resin was filtered and washed with DMF, MeOH, and CH2Cl2 several times. The desired compound was cleaved from a solid support by treatment with trifluoroacetic acid (TFA) for 1.5 h. The crude product was directly purified by preparative RP-HPLC with a gradient of 5-100% CH3CN in water (0.1% TFA) over 85 min.

Provenance & Evidence