Table 2 Optimization for in situ generation of (1H-indol-3-yl)methyl electrophile from 7a and its nucleophilic substitution with NaN₃ in a microflow reactor.

^aThe reagent quantities were changed based on the reaction mechanism. Theoretically, 1 equiv. of PBr₃, PCl₃, or POCl₃ can convert 3 equiv. of alcohol to the alkyl halide, 1 equiv. of SOBr₂, or SOCl₂ can convert 2 equiv. of alcohol, and 1 equiv. of AcBr, AcCl, Ac₂O, Tf₂O, MsCl, or TsCl can convert equimolar quantities of alcohol.
^bYields were determined by ¹H NMR analysis using 1,1,2-trichloroethane as an internal standard.
^cNEt₃ was added with a solution of 7a instead of a solution of NaN₃.
^dThe reaction was carried out at 0 °C.
^e0.0500 M solution of 7a was used.
^fThree independent experiments were performed.
^gReaction mixture was magnetically stirred (1000 rpm) under batch conditions.

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