Allyl bromide → HCID 58382078, compound

Participants

Reaction Conditions

Reaction Steps

The 4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (3.10 g, 10.0 mmol, Preparation #1, Step A) in THF (40 mL) was cooled to about −75° C. then sec-BuLi (1.4 M in hexane, 14.3 mL, 20.0 mmol) was added slowly keeping the temperature below −65° C. The mixture was stirred at about −75° C. for about 45 min then copper(I) cyanide (0.090 g, 1.00 mmol) was added. The mixture was stirred for about 5 min then allyl bromide (2.61 mL, 30.1 mmol) was added drop-wise. After about 10 min saturated aqueous NaHCO3 (20 mL) and EtOAc (50 mL) were added to the mixture. The mixture was partitioned between water (20 mL) and EtOAc (50 mL). The layers were separated then the aqueous layer was extracted with EtOAc (25 mL). The combined organic layers were washed with saturated aqueous NaHCO3 (40 mL) then dried over anhydrous MgSO4, filtered and concentrated in vacuo. The material was purified by flash chromatography on 120 g silica gel with 98:2 heptane/EtOAc as an eluent to give 5-allyl-4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (3.2 g, 91%): LC/MS (Table 2, Method g) Rt=2.63 min; MS m/z 349 (M+H)+.

Provenance & Evidence