These common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, 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. SDS of cas: 16066-84-5
Example 25 2′-(2,6-difluoro-3,5-dimethoxyphenyl)-6′-(methylamino)-1′,2′-dihydro-3’H-spiro[cyclopropane-1,4′-[2,7]naphthyridin]-3′-one To a stirred solution of 6′-chloro-2′-(2,6-difluoro-3,5-dimethoxyphenyl)-1′,2′-dihydro-3’H-spiro[cyclopropane-1,4′-[2,7]naphthyridin]-3′-one (Example 23, Step 6: 90.0 mg, 0.236 mmol) and tert-butyl methylcarbamate (89.5 mg, 0.682 mmol) in 1,4-dioxane (3 mL) were added sequentially dicyclohexyl(2′,4′,6′-triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine (BrettPhos, Aldrich, catNo.718742: 24.4 mg, 0.0455 mmol), sodium tert-butoxide (52.4 mg, 0.546 mmol), and palladium acetate (10.2 mg, 0.0455 mmol) at room temperature. The resulting mixture was purged with N2 and heated to 90 C. After stirring for 45 minutes at 90 C., the reaction mixture was cooled to ambient temperature and the volatiles were removed in vacuo. The residue was dissolved in DCM (1 mL) then TFA (1 mL) was added. After stirring at room temperature for 1 hour, the reaction mixture was concentrated and the crude was purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 60 mL/min) to give the desired product (32 mg) as its TFA salt. LC-MS calculated for C19H20F2N3O3 [M+H]+ m/z: 376.1. found 376.2. 1H NMR (500 MHz, DMSO-d6): delta 7.90 (s, 1H), 7.07 (t, J=10.0 Hz, 1H), 6.46 (s, 1H), 4.80 (s, 2H), 3.89 (s, 6H),), 2.90 (s, 3H) 1.79 (dd, J=10.0 Hz, 5.0 Hz, 2H), 1.56 (dd, J=10.0 Hz, 5.0 Hz, 2H) ppm.
The synthetic route of tert-Butyl methylcarbamate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Sun, Yaping; Lu, Liang; Yao, Wenqing; Zhuo, Jincong; Wu, Liangxing; Xu, Meizhong; Qian, Ding-Quan; He, Chunhong; Zhang, Fenglei; US2014/315902; (2014); A1;,
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