Sodium hydride → HCID 58382200, compound

Participants

Reaction Steps

The 4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (5.00 g, 17.9 mmol, US 2006128661 Example 1) in DMF (50 mL) was treated with 60 wt % NaH (0.790 g, 19.7 mmol) then stirred for about 15 min. The TIPSCl (4.18 mL, 19.8 mmol) was then added to the mixture and the mixture was stirred for about 30 min. The solvents were evaporated under reduced pressure then the material was partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (50 mL). The layers were separated then the aqueous layer was extracted with EtOAc (25 mL). The combined organics were washed with water (25 mL) then brine (25 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography using a 120 g silica column and eluting with heptane to give 4-chloro-3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (5.34 g, 68%): LC/MS (Table 2, Method g) Rt=2.58 min; MS m/z 435 (M+H)+.

Provenance & Evidence