Dimethylformamide → HCID 67102595, compound

Participants

Reaction Steps

To a DMF (6 mL) solution of 4-Amino-N-(6-bromo-1H-indol-5-yl)-benzenesulfonamide (750 mg, 2.05 mmol) was added NaHMDS (2.77 mL, 1M in THF) and stirred for 20 min at RT. Methyl iodide (0.153 mL, 2.46 mmol) was added in a single portion. After stirring for 2.5 hr at RT TLC analysis (10% MeOH/dichloromethane) shows two new less-polar products. The reaction mixture was poured into 75 mL of saturated sodium bicarbonate solution and extracted with EtOAc (2×50 mL). The organic layers were combined, washed with brine, dried over MgSO4, and concentrated to give a yellow oil. Chromatography (SiO2; 0%-5% MeOH/dichloromethane) gives 4-amino-N-(6-bromo-1-methyl-1H-indol-5-yl)-N-methyl-benzenesulfonamide as the less-polar product (MS=394, 396 [M+H]) and 4-amino-N-(6-bromo-1H-indol-5-yl)-N-methyl-benzenesulfonamide (only 85% pure) as the more-polar product (MS=380, 382 [M+H]). The corresponding boronates were separately prepared following general procedures as described in these Examples: 4-Amino-N-methyl-N-[1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indol-5-yl]-benzenesulfonamide: (MS=442 [M+H]); 4-Amino-N-methyl-N-[6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indol-5-yl]-benzenesulfonamide, following chromatography (SiO2; 1%-5% MeOH/dichloromethane): (MS=428 [M+H]).

Provenance & Evidence