Uses
(5-Methoxypyridin-2-yl)methanol is used in preparation of substituted pyrrolopyridinones as HPK1 antagonists and uses thereof.
Synthesis
Compound 12 (CAS: 75342-32-4, 1.40 g, 7.7 mmol) was used as raw material, which was dissolved in methanol (30 mL) and excess potassium hydroxide was added. The reaction mixture was heated to reflux for 2 hours. After completion of the reaction, the solvent was removed by rotary evaporator under reduced pressure. The residue was extracted by partitioning with dichloromethane (20 mL) and water (20 mL). The organic phase was separated, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give compound 13 (5-methoxypyridine-2-methanol) as a light yellow oil (1.00 g, 93% yield). The product was characterized by 1H NMR (CDCl3): δ 1.82 (s, 1H), 3.87 (s, 3H), 4.70 (s, 2H), 7.18-7.24 (m, 2H), 8.25 (d, 1H, J = 2.8 Hz); GC/MS analysis showed m/z 140 (M++1, 3%), 139 (M+, 44%), 138 ( 100%), 110 (71%).
References
[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3913 - 3924
[2] Patent: US6194437, 2001, B1
[3] Patent: US2006/14945, 2006, A1. Location in patent: Page/Page column 40
[4] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 438 - 450
[5] Patent: WO2007/120729, 2007, A2. Location in patent: Page/Page column 40
