Hydrochloric Acid → HCID 58382001, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloro-3-ethyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (1.5 g, 4.45 mmol) in THF (25 mL) was cooled to about −70° C. then the sec-BuLi (1.4 M in cyclohexane, 6.36 mL, 8.90 mmol) was added over about 10 min. The mixture was stirred for about 1.25 h at about −70° C. then DMF (1.00 mL, 13.4 mmol) was added over about 5 min. The mixture was stirred for about 30 min then HCl (4.0 M in 1,4-dioxane, 1.11 mL, 4.45 mmol) was added. The mixture was allowed to warm to rt then saturated aqueous NaHCO3 (50 mL) and EtOAc (50 mL) were added. The layers were separated then the aqueous layer was extracted with EtOAc (25 mL) then the combined organics were extracted with saturated aqueous NaCl (25 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The material was purified on a 80 g silica gel column with 9:1 heptane/EtOAc as an eluent to give 4-chloro-3-ethyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1.48 g, 91%): LC/MS (Table 2, Method g) Rt=2.44 min; MS m/z 365 (M+H)+.

Provenance & Evidence