Related Products of 20780-72-7, A common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, molecular formula is C8H4BrNO2, 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.
General Procedure 3 Suzuki Coupling of 4-bromoindoline-2,3-dione Derivatives with Trifluoroborate Potassium Salts [0344] 4-Bromoisatin (1 eq) was added to a solution of the potassium trifluoroborate salt (1.4 eq), K3PO4 (3.6 eq) and degassed solvent. The reaction mixture was degassed and Pd(PPh3)2Cl2 or Pd(dppf)2Cl2 (0.1 eq) was added. The reaction vessel was sealed and heated by microwave irradiation (Biotage Initiator) for 4 h at 130° C. The reaction mixture was cooled to rt, diluted with EtOAc (10 mL/mmol substrate) and filtered through Celite®. The organic solution was washed with brine (10 mL/mmol substrate) and the resulting aqueous layer was further extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product which was purified as specified below. 4-(o-Tolyl)indoline-2,3-dione Following General Procedure 3,4-bromoisatin (100 mg, 0.44 mmol), potassium 2-methyphenyltrifluoroborate (123 mg, 0.62 mmol), K3PO4 (338 mg, 1.59 mmol) and Pd(PPh3)2Cl2 (31 mg, 0.04 mmol) in THF/H2O (3:1, 3 mL) gave the crude reaction mixture, which was purified via flash column chromatography (eluent 30-40° C. petrol/acetone, 4:1) to afford the product as an orange solid (65 mg, 59percent). deltaH (500 MHz, DMSO-d6) 2.15 (3H, s), 6.93 (2H, m), 7.14 (1H, d, J=7.6 Hz), 7.20-7.26 (1H, m), 7.30 (1H, d, J=7.3 Hz), 7.32-7.37 (1H, m), 7.56 (1H, app t, J=7.9 Hz), 8.84 (1H, br s) 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 mp 161-162° C.
The synthetic route of 20780-72-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Christou, Ivy; Cross, Rebecca Lillian; Gianella-Borradori, Matteo; Greaves, David Robert; Russell, Angela Jane; Wynne, Graham Michael; US2014/378451; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem