Isatin → HCID 553397, compound

Participants

Reaction Conditions

Reaction Steps

In a 250 mL flame dried round bottom flask equipped with a stir bar, tert-butyldimethylsilyl chloride (4.5 g, 30 mmol) is dissolved in 150 mL dichloromethane. To this solution, in a single portion, isatin (2.2 g, 15 mmol) and 4-dimethylaminopyridine (0.18 g, 1.5 mmol) are added. The flask is sealed with a rubber septum and purged with nitrogen. Triethylamine (6.3 mL, 45 mmol) is added in one portion through a syringe and mixture is allowed to stir for 24 h at 22° C. The volatiles are removed in vacuo and the resultant dark orange solid is purified by silica gel chromatography (hexanes to 1:1 hexanes:dichloromethane to dichloromethane) to afford an orange solid, which is recrystallized from hot EtOH (details below) to afford 14a (2.6 g, 9.9 mmol, 67% yield) as an orange crystalline solid. Please note that for long-term storage, N-tert-butyldimethylsilyl protected isatins should be kept under an inert atmosphere at −15° C. 1-(tert-Butyldimethylsilyl)indoline-2,3-dione (14a): M.p.=123-124° C. IR (neat): 2929 (w), 2853 (w), 1731 (s), 1603 (m), 1589 (m), 1463 (m), 1325 (m), 1252 (m), 1170 (m), 1139 (m), 927 (m), 835 (s), 796 (m), 752 (s), 686 (m), 466 (m), 424 (m) cm−1; 1H NMR (400 MHz, CDCl3): δ 7.63-7.61 (1H, m), 7.53-7.49 (1H, m), 7.10-7.03 (2H, m), 1.02 (9H, s), 0.56 (6H, s); 13C NMR (100 MHz, CDCl3): δ 184.2, 164.9, 155.4, 138.3, 125.6, 123.4, 120.0, 115.1, 26.4, 19.7, −3.3; HRMS Calcd for C14H20NO2Si [M+H]+: 262.12633. Found: 262.12608.

Provenance & Evidence