Sodium Iodide → HCID 58382025, compound

Participants

Reaction Steps

7-(5-Methoxy-1-methyl-1H-indol-3-yl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (1.00 g, 3.02 mmol [WO2009/152133, Example #42]) and NaH (60 wt % in mineral oil, 0.200 g, 5.00 mmol) were added to DMF (40 mL) then the mixture was stirred at rt for about 10 min. Then NaI (0.068 g, 0.453 mmol) and di-tert-butyl chloromethyl phosphate (1.60 g, 6.19 mmol, [Journal of Medicinal Chemistry (2008), 51(5), 1111-1114]) were added then the mixture was warmed to about 60° C. for about 45 min. The mixture was cooled to rt then concentrated under reduced pressure. The material was partitioned between water (50 mL) and EtOAc (50 mL). The organic layer was isolated and the aqueous layer was extracted with EtOAc (2×50 mL) then DCM (2×30 mL). The combined organics were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The material was purified using an 80 g silica column and eluting with EtOAc to give di-tert-butyl (7-(5-methoxy-1-methyl-1H-indol-3-yl)-1-methylpyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-6(1H)-yl)methyl phosphate (0.486 g, 29%): LC/MS (Table 2, Method a) Rt=2.68 min; MS m/z 554 (M+H)+.

Provenance & Evidence