Stannane, tributyl(1-ethoxyethenyl)- → HCID 86689828, compound

Participants

Reaction Conditions

Reaction Steps

A high-pressure tube was charged with tributyl(1-ethoxyvinyl)stannane (7.75 g, 21.45 mmol) and tert-butyl 5-chloropyrrolo[3,2-b]pyridine-1-carboxylate (4.17 g, 16.50 mmol) in degassed DMF (64.0 mL) and Pd(PPh3)4 (1.9 g, 1.65 mmol) was added in one batch. The tube was closely tightly and the reaction mixture was stirred at 100° C. under N2 for 2 d. The reaction mixture was cooled, diluted with EtOAc (350 mL), and filtered through a pad of Celite® to remove solid Pd. The filtrate was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was dissolved in anhydrous THF (80.2 mL), and 2N HCl (41 mL) was added. The reaction mixture was stirred at RT under N2 for 16 h, poured into 10% aq. NaOH solution (100 mL) and then extracted with EtOAc (3×150 mL). The combined organic phases were washed with water and brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by SiO2chromatography eluting with EtOAc/heptane to afford 1.69 g (64.1%) of 1-(1H-pyrrolo[3,2-b]-pyridin-5-yl)ethanone as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.49 (s, 1H), 7.99 (d, J=8.5 Hz, 1H), 7.74 (d, J=8.5 Hz, 1H), 7.54 (t, J=3.0 Hz, 1H), 6.86 (s, 1H), 2.80 (s, 3H); MS (ESI) m/z: 161.3 [M+1]+.

Provenance & Evidence