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Substitution (Cl)



Example 1

To a solution of the indole (A) (0.300 g, 0.92 mmol) in THF (30 mL) was added NaHMDS (1 M in THF, 0.93 mL, 0.93 mmol) at -78 C. The mixture was stirred at -78 C for 20 min, then at RT for 1 h. The alkyl chloride (B) (171 mg, 1.86 mmol) was added, and the reaction mixture was stirred at RT for another 18 h. The mixture was quenched with ice-H2O and extracted with EtOAc (3 x 30 mL). The combined organics were dried (Na2SO4) and concentrated to provide the product which was used in the next step without further purification. [0.300 g, 84%]

[Patent Reference: WO2016100281, page 245, (10.3 MB)]