Dimethylformamide → HCID 86609780, compound

Participants

Reaction Conditions

Reaction Steps

Trityl chloride (3.90 g, 14 mmol), 4-DMAP (2.08 g, 17 mmol) and 2-bromo-5-hydroxymethylpyridine 33 (1.88 g, 10 mmol) (Ellingboe, J. W., et al., J. Med. Chem. 1994, 37, 542–550) were dissolved in DMF (15 mL) and the solution was stirred at 80° C. for 48 hours. A white precipitate formed during this time. After cooling, the mixture was diluted with NaHCO3 (sat., 25 mL) and extracted with EtOAc (3(50 mL). The combined extract was washed with brine, with a few drops of NaOH (1 M) added (2(100 mL). After drying and evaporation, the solid residue was purified by flash chromatography (silica, hexanes:EtOAc 15:1) to yield 34 as a white solid (4.46 g, 100%). TLC Rf=0.30 (silica, hexanes:EtOAc 15:1); IR (film) vmax 3057, 1448, 1086, 764, 700, 632 cm−1; MALDI-FTMS m/z 430.0792 (MH+), calcd for C25H21BrNO 430.0801.

Provenance & Evidence