Water → 7-(6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine

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Reaction Conditions

Reaction Steps

To a flask was added 3-bromo-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole (0.250 g, 1.33 mmol, Apollo) and THF (3 mL). The mixture was cooled to about −30° C. and then i-PrMgBr (2.0 M in THF, 0.735 mL, 1.47 mmol) was added. After about 15 min, in a separate flask, zinc chloride (0.219 g, 1.604 mmol) was dissolved in THF (3 mL) and then the solution was added dropwise to the mixture. After about 30 min at about −20° C., 7-iodo-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.250 g, 0.553 mmol; Preparation #1) and Pd(Ph3P)4 (0.093 g, 0.080 mmol), dissolved in DMF (2 mL) were then added to the mixture and it was then heated to about 80° C. for about 90 min. Water was added (30 mL) and solids were collected by filtration and dried under reduced pressure to provide 7-(6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.578 g, 100%): LC/MS (Table 2, Method c) Rt=1.27 min; MS m/z 433 (M+H)+.

Provenance & Evidence