Acetic Acid → HCID 58382237, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropylamine (0.260 mL, 1.83 mmol) in THF (5 mL) was cooled to about −70° C. then the n-BuLi (1.6 M in hexanes, 1.04 mL, 1.67 mmol) was added drop-wise. The mixture was stirred at about −70° C. for about 15 min then allowed to warm to about 20° C. The resulting solution was added drop-wise to the 8-ethyl-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.295 g, 0.832 mmol) in THF (5 mL) at about −60 to −70° C. then the mixture was stirred for about 1 h. Iodine (0.239 g, 0.942 mmol) in THF (2 mL) was added drop-wise to the mixture and then it was stirred at about −70° C. for about 1 h. The reaction was treated with AcOH (0.143 mL, 2.50 mmol) then about 1 mL of saturated aqueous NH4Cl was added then the solution was warmed to rt. The mixture was diluted with EtOAc (50 mL) and water (20 mL) then the layers were separated. The organic layer was washed with saturated aqueous NaCl (20 mL) then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The material was purified on a 10 g silica gel column with 94:6 DCM/EtOAc as an eluent to give 8-Ethyl-7-iodo-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.155 g, 39%): LC/MS (Table 2, Method a) Rt=2.78 min; MS m/z 481 (M+H)+.

Provenance & Evidence