Sodium Bicarbonate → HCID 86659281, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(5-chloro-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-(1-(methoxymethoxy)cyclobutyl)thiazole (580 mg, 0.921 mmol) (Example 1F), 3-fluoro-4-formylphenylboronic acid (309 mg, 1.842 mmol), and bis(triphenylphosphine)palladium dichloride (32.3 mg, 0.046 mmol) in N,N-dimethylformamide (12 ml) was added saturated aqueous sodium bicarbonate solution (12 mL). The mixture was heated to 65° C. under an atmosphere of nitrogen for about 90 minutes. The reaction mixture was cooled to room temperature, and diluted with water (about 50 mL) and saturated brine solution (about 25 mL). The aqueous layer was extracted with ethyl acetate (3×30 mL), and the combined organics were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 0 to 30% ethyl acetate in hexane, to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.30 (s, 1H), 8.63-8.60 (m, 1H), 8.23 (s, 1H), 7.95 (t, 1H), 7.81-7.72 (m, 3H), 7.65 (dd, 1H), 7.40 (d, 2H), 7.14 (d, 1H), 4.76 (s, 2H), 2.71-2.54 (m, 2H), 2.35 (s, 3H), 2.01-1.88 (m, 3H). MS APCI(+) m/z 626.42 [M+H]+.

Provenance & Evidence