Sodium Carbonate → HCID 57537662, compound

Participants

Reaction Steps

A mixture of 2-(5-Bromo-pyridin-3-yl)-2-hydroxy-N,N-dimethyl-acetamide (40 mg, 0.15 mmol), bis(pinacol)diborane (47 mg, 0.18 mmol), potassium acetate (45 mg, 0.46 mmol), and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichlormethane adduct (6 mg, 0.007 mmol) in dimethylacetamide (1 mL) was irradiated in a Personal Chemistry Optimizer at 120° C. for 30 min. 5-Bromo-3-(2-methoxy-phenyl)-4-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (39 mg, 0.077 mmol), sodium carbonate solution (2M in water, 0.39 mL, 0.77 mmol), and additional 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichlormethane adduct (3 mg, 0.03 mmol) was added and the mixture was irradiated for an additional 30 min at 120° C. Sodium sulfate was added to the crude reaction mixture and the solids were filtered over Celite. The solids were rinsed with ethyl acetate and the combined filtrate was concentrated. The solids were resuspended in ethyl acetate, filtered through a plug of silica and the eluent was concentrated. The resulting oil was dissolved in trifluoroacetic acid (2 mL) and shaken for 5 min. The solution was concentrated and the mixture was redissolved in dimethyl sulfoxide and ethylenediamine. Purification by mass triggered reverse phase HPLC afforded 2-Hydroxy-2-{5-[3-(2-methoxy-phenyl)-4-trifluoromethyl-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-N,N-dimethyl-acetamide (2.5 mg, 0.005 mmol, 7% yield). 1H NMR (500 MHz, MeOH-d4) δ 12.55 (bs, 1H), 8.60 (s, 1H), 8.51 (s, 1H), 8.24 (s, 1H), 7.72 (s, 1H), 7.71 (m, 1H), 7.31 (m, 1H), 7.24 (dd, J=7 Hz, J2=2 Hz, 1H), 6.99 (d, J=7.5 Hz, 1H), 6.95 (td, J=7.5 Hz, J2=1 Hz, 1H), 5.8 (bs, 1H), 5.56 (s, 1H), 3.65 (s, 3H), 2.90 (m, 3H), 2.84 (s, 3H). MS: m/z 471.0 (M+H+).

Provenance & Evidence