Sodium Hydroxide → 8-((1H-imidazol-5-yl)(pyridin-2-yl)methyl)quinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of pyridin-2-yl(quinolin-8-yl)(1-trityl-1H-imidazol-5-yl)methanol (Intermediate 14) (385 mg, 0.70 mmol) in 57% aqueous HI (10 mL) and iPrOH (2 mL) was added red phosphorus (219 mg, 7.0 mmol) in a resealable tube was heated at 160° C. for 16 h. The mixture was then cooled to room temperature and poured into ice-water, which was then basified with NaOH and diluted with CHCl3. The residue was isolated in a typical aqueous workup using CHCl3 and purified by MPLC with 5 to 15% MeOH:CH2Cl2 to give 8-((1H-imidazol-5-yl)(pyridin-2-yl)methyl)quinoline, (658) as a solid, 236 mg (61% in two steps). 1HNMR (CD3OD, 300 MHz) δ 8.82 (dd, J=1.8, 4.5 Hz, 1H), 8.43 (dd, J=1.8, 5.7 Hz, 1H), 8.28 (dd, J=1.8, 8.4 Hz, 1H), 7.83 (dd, J=4.0, 7.8 Hz, 1H), 7.73-7.70 (m, 2H), 7.68-7.43 (m, 3H), 7.25-7.21 (m, 2H), 7.03 (s, 1H), 6.52 (s, 1H).

Provenance & Evidence