Hexamethylditin → N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.2 g, 468 μmol) and hexamethylditin (215 mg, 655 mmol) in toluene (2.5 mL) was added Pd(Ph3P)4 (54 mg). After bubbling nitrogen through the reaction mixture for 15 min, it was heated to 95° C. After 1.5 h, 7-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine and Pd(Ph3P)4 (108 mg, 93.6 μmol) were added. After 72 h the reaction mixture was cooled, filtered through celite, and concentrated in vacuo. Purification by chromatography (silica, 24 g Analogix column, 0-40% ethyl acetate in hexanes) gave N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.13 g, 47%). 1H NMR (CDCl3) δ: 9.01 (s, 1H), 8.46 (d, J=5.3 Hz, 1H), 8.34 (s, 1H), 8.13 (s, 1H), 7.68 (d, J=5.3 Hz, 1H), 7.41 (d, J=3.0 Hz, 1H), 6.69 (d, J=3.3 Hz, 1H), 5.74 (s, 2H), 5.51 (s, 2H), 3.59 (dd, J=8.9, 7.7 Hz, 2H), 2.82-2.89 (m, 2H), 1.42 (s, 9H), 0.92-0.99 (m, 2H), 0.41-0.47 (m, 2H), −0.02 (s, 9H), −0.27 (s, 9H).

Provenance & Evidence