Synthetic Route of 20780-72-7, These common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, 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 solution of 4-bromoisatin 30 (100 mg, 0.44 mmol) in degassed THF/water (3:1, 2.5 mL) was added potassium 2-methylphenyltrifluoroborate (114 mg, 0.62 mmol) and K3PO4 (338 mg, 1.59 mmol) followed by Pd(PPh3)2Cl2 (31 mg, 0.04 mmol). The reaction vessel was sealed and heated by microwave irradiation for 4 h at 130 °C. The reaction mixture was cooled to rt, diluted with EtOAc (5 mL) and filtered through Celite®. The organic solution was washed with brine (5 mL) and the resulting aqueous layer was further extracted with EtOAc (2*). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The product was purified via flash column chromatography (eluent 40-60 °C, petrol/EtOAc, 4:1) to afford the title compound (41) as an orange solid (40 mg, 42percent); mp 161-162 °C; numax (solid) 3249, 3017, 2926, 1727, 1603, 1480; deltaH (500 MHz, DMSO-d6) 2.15 (3H, s, CH3), 6.93 (2H, m, C(5)H and C(7)H), 7.14 (1H, d, J = 7.6 Hz, C(6′)H), 7.20-7.26 (1H, m, C(4′)H), 7.30 (1H, d, J = 7.3 Hz, C(3′)H), 7.32-7.37 (1H, m, C(5′)H), 7.56 (1H, app t, J = 7.9 Hz C(6)H), 8.84 (1H, br s, NH); deltaC (125 MHz, DMSO-d6) 19.7, 111.2, 115.7, 125.6, 126.3, 128.6, 128.8, 130.1, 135.7, 136.4, 137.9, 142.8, 149.3, 159.2, 182.0; m/z (ESI-) 236 ([M-H]-, 60percent); HRMS (ESI-) C15H10NO2- ([M-H]-) requires 236.0717; found 236.0719.
Statistics shows that 4-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 20780-72-7.
Reference:
Article; Gianella-Borradori, Matteo; Christou, Ivy; Bataille, Carole J.R.; Cross, Rebecca L.; Wynne, Graham M.; Greaves, David R.; Russell, Angela J.; Bioorganic and Medicinal Chemistry; vol. 23; 1; (2015); p. 241 – 263;,
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