Reference of 32692-19-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 32692-19-6 name is 5-Nitroindoline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
A dry Schlenk tube was charged with Cs2C03 (266 mg, 0.816 mmol). The tube was evacuated for 30 min and then flushed with argon and 9 (150 mg, 0.272 mmol) was added to the tube, followed by Pd2(dba)3 (2.8 mg, 0.003 mmol) and X-Phos (6.5 mg, 0.014 mmol). The mixture was dissolved in dry dioxane (5 mL) and the solution was degassed in an ultrasonic bath for 20 min. Then 5-nitroindoline (67.3 mg, 0.41 mmol) was added and the mixture was stirred for 53 h at 80C. TLC (petrol ether/EtOAc 3:1 ) and mass spectroscopy indicated the formation of partially deacetylated mannoside during the progress of the reaction. Therefore, dry pyridine (2 mL) and dry acetic anhydride (1 mL) were added 50 h after the reaction started to regain fully protected mannoside. Then EtOAc (30 mL) and satd. aq. NaHC03 solution (50 mL) were added to the reaction mixture. The layers were separated and the organic phase was washed with brine (2 x 50 mL). The aqueous layers were extracted with EtOAc (3 x 30 mL). The combined organic layers were dried with Na2S04, filtered and concentrated under reduced pressure. The residue was purified with silica gel chromatography (petrol ether/EtOAc, 10:1 -1 :1 ) to give 10 (128 mg, 80%) as an orange solid.1H NMR (CDCI3): delta 2.02, 2.20 (2s, 12H, 4 OAc), 3.21 (t, J = 8.5 Hz, 2H, CH2), 4.1 1 (m, 4H, CH2, H-6a, H-5), 4.26 (dd, J = 7.3 Hz, 1 H, H-6b), 5.37 (t, J = 9.9 Hz, 1 H, H-4), 5.43 (s, 1 H, H-2), 5.53 (m, 2H, H-1 , H-3), 6.84 (d, J = 8.3 Hz, 1 H, Ar), 6.98 (m, 3H, Ar), 7.30 (t, J = 8.1 Hz, 1 H, Ar), 8.00 (s, 1 H, Ar), 8.05 (d, J = 8.8 Hz, 1 H, Ar).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Nitroindoline, and friends who are interested can also refer to it.
Reference:
Patent; UNIVERSITY OF BASEL; ERNST, Beat; WO2012/164074; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem