Sodium Carbonate → HCID 57537527, compound

Participants

Reaction Steps

Into a 20 mL Personal Chemistry microwave reaction vial were added 2-Amino-N,N-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinamide (1.55 g, 5.35 mmol), 5-Bromo-4-chloro-3-(4-chloro-2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (1.58 g, (3.15 mmol), bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichloromethane adduct (129 mg, 0.158 mmol), sodium carbonate solution (3.15 mL, 6.30 mmol, 2.0 M solution in water) and N,N-dimethylformamide (15 mL). The vial was purged with nitrogen, sealed, and irradiated in a Personal Chemistry Optimizer at 120° C. for 30 minutes. The mixture was concentrated in vacuo. The crude was taken up in dichloromethane (150 mL) and washed with aqueous saturated sodium carbonate solution (1×150 mL) and brine (1×150 mL). The organ phase was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes to afford 2-Amino-5-[4-chloro-3-(4-chloro-2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide (1.02 g, 1.74 mmol, 55% yield). 1H-NMR [500 MHz, d6-DMSO] δ: 8.26 (s, 1H), 8.06 (d, 1H), 7.72 (s, 1H), 7.48 (d, 1H), 7.26 (d, 1H), 7.11 (d, 1H), 7.03 (dd, 1H), 6.18 (s, 2H), 5.66 (s, 2H), 3.71 (s, 3H), 3.59 (t, 2H), 2.94 (s, 6H), 0.85 (s, 2H), −0.08 (s, 8H); MS [MH+] m/z: 486

Provenance & Evidence