Sodium hydride → HCID 58382200, compound

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)+.

1. stirringthe mixture was stirred for about 30 min
2. customThe solvents were evaporated under reduced pressure
3. customthe material was partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (50 mL)
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with EtOAc (25 mL)
6. washThe combined organics were washed with water (25 mL)
7. dry with materialbrine (25 mL), dried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel chromatography
11. washeluting with heptane

ORD record

ord-de1553cd484d47e7901d65214a23fd37

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785639B2