Electric Literature of 60781-83-1 ,Some common heterocyclic compound, 60781-83-1, molecular formula is C11H10N2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
To a RT solution of 4-phenylpyridin-2-amine (8 mg, 0.044 mmol) in THF (0.5 mL) was added NaH (2 mg, 0.033 mmol, 60% in mineral oil), and the mixture was stirred at RT for 30 min. Intermediate 1 (10 mg, 0.022 mmol) in THF (0.2 mL) was added and the reaction mixture was stirred at RT for 4 h, after which THF (0.8 mL)/H20 (0.4 mL)/ MeOH (0.4 mL) and LiOH.H20 (5 mg, 0.11 mmol) were added and the mixture was stirred overnight at RT. Volatiles were removed in vacuo and the residue was diluted with H20 (5 mL); the mixture was adjusted with 1N aq. HC1 to pH ~5 and extracted with EtOAc (3 x 5 mL). The combined organic extracts were washed with brine (2 mL), dried (MgSCL), and concentrated in vacuo. The crude product was purified by preparative LC/MS: Column: Waters XBridge Cl 8, 19 x 200 mm, 5-pm particles; Guard Column: Waters XBridge C18, 19 x 10 mm, 5-pm particles; Mobile Phase A: 5:95 MeCN:H20 with 0.1% TFA; Mobile Phase B: 95:5 MeCN:H20 with 0.1% TFA; Gradient: 50-90% B over 20 min, then a 5-min hold at 100% B; Flow: 20 mL/min. The combined fractions containing the desired product were concentrated in vacuo by centrifugal evaporation to give the title compound (3.1 mg, 6.0 pmol, 27 % yield). LCMS, [M + H]+ = 499.3. NMR (500 MHz, DMSO-de) d 8.05 (d, ,7=5.6 Hz, 1H), 7.87 (d, ,7=8.5 Hz, 1H), 7.51 (d, ,7=8.6 Hz, 1H), 7.46 – 7.40 (m, 2H), 7.38 – 7.32 (m, 3H), 6.85 – 6.80 (m, 2H), 5.04 (d, J=5.5 Hz, 2H), 4.79 – 4.72 (m, 1H), 4.14 (s, 3H), 2.59 – 2.54 (m, 1H), 2.39 (s, 3H), 2.01 – 1.45 (m, 8H). hLPAi IC5o = 32 nM.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 60781-83-1, 4-Phenylpyridin-2-amine, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; WANG, Ying; CHENG, Peter Tai Wah; SHI, Jun; TAO, Shiwei; CORTE, James R.; FANG, Tianan; LI, Jun; KENNEDY, Lawrence J.; KALTENBACH, III, Robert F.; JUSUF, Sutjano; (316 pag.)WO2019/126093; (2019); A1;,
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