Pyridine → HCID 11655774, compound

Participants

Reaction Conditions

Reaction Steps

(E)-2-((tert-butyldimethylsilyloxy)methyl)-N-(3-tert-butylphenyl)-3-(3-(2-(4,5-dihydro-1H-imidazol-2-yl)pyridin-4-yloxy)phenyl)acrylamide (107 mg, 0.18 mmol) was dissolved in a 1:1 mixture of THF/pyridine (3 mL). The reaction mixture was cooled to 0° C. and 20 drops of HF/pyridine were added. The reaction was sealed and allowed to warm to rt over 5 h. The mixture was diluted with EtOAc and washed with sat. NaHCO3, dried over Na2SO4, filtered, and concentrated. Purification by column chromatography (SiO2, 0-10% MeOH with 1% NH4OH in DCM) provided B-140 (32 mg). LCMS, FA: Rt=1.21 min, [MH+ 471.0]. 1H NMR (300 MHz, d4-MeOH): δ 8.48 (d, 1H), 7.68 (t, 1H), 7.56-7.51 (m, 3H), 7.48-7.44 (m, 1H), 7.41 (d, 1H), 7.31 (t, 1H), 7.25 (t, 1H), 7.19-7.15 (m, 2H), 7.08-7.05 (dd, 1H), 4.52 (s, 2H), 3.75 (s, 4H), and 1.32 (s, 9H).

Provenance & Evidence