As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO199,mainly used in chemical industry, its synthesis route is as follows.,701-16-6
[0589] Compound 82: To a stirred solution of Comp-82b (0.1 g, 0.66 mmol) in mixture of THF (5 mL) and ffiuOH (1 mL) was added r-BuOK (0.2 g, 1.98 mmol) and the reaction mixture was stirred for 10 min. Comp-50c(0.1 g, 0.66 mmol) was added portion wise and the reaction mixture was stirred at room temperature for 16 h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was quenched with H20 (5 mL) and extracted with EtOAc (10 mL X 2). The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to get crude. The crude obtained was purified by prep HPLC to afford (E)-2-(2-(l-cyclopentyl-2,5- dimethyl-lH-pyrrol-3-yl)vinyl)-5-fluorobenzo[d]oxazole (82; 0.08 g, 40%) as white solid. (1026) [0590] HPLC Purity: 99.8% (1027) [0591] MS (ESI) m/e [M+H]+ Rt %: 325.2/2.47/99.4% (1028) [0592] 1H NMR (400 MHz, DMSO- d6) delta 1.62- 1.64 (m, 2 H), 1.82- 1.84 (m, 4 H), 1.98 – 2.08 (m, 2 H), 2.24 (s, 3 H), 2.36 (s, 3 H), 4.54 – 4.67 (m, 1 H), 6.26 (s, 1 H), 6.50 (d, J=15.65 Hz, 1 H), 7.10 – 7.19 (m, 1 H), 7.46 (dd, J=8.80, 2.45 Hz, 1 H), 7.62 – 7.64 (m, 1 H), 7.67 (d, J=15.65 Hz, 1 H).
With the complex challenges of chemical substances, we look forward to future research findings about 5-Fluoro-2-methylbenzo[d]oxazole,belong benzoxazole compound
Reference£º
Patent; ALPINE ANDROSCIENCES, INC.; PATIL, Santhosh N.; SARMA, Bugga VNBS; (148 pag.)WO2019/152731; (2019); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem