Using the above-described 24-well plate (Figure ), the coupling efficiency of a diverse selection of 80 Nheteroaromatic compounds containing different scaffolds relevant to medicinal chemistry (e.g., pyridines, pyrimidines and indoles, F1-F80, SI4.1) with 59 carboxylic acids (e.g., linear, branched, cyclic, heterocyclic, aromatic, A1-A59, SI4.2) following the Miniscitype alkylation mechanism was assessed. The reaction setup (automated liquid handling of prepared stock solutions) and execution (heating and stirring) in glass vials on a parallel screening plate were conducted under a normal atmosphere. Upon completion of the reaction, the solvents were removed by evaporation, followed by automated resuspension of the residues in MeCN/H 2 O and dilution to a defined concentration for LC-MS analysis using automated liquid handling. The resulting data were subjected to an automated reaction data analysis pipeline to rapidly determine all components within the mixture . The standardized output of the data in SURF allowed direct visualization of the reaction outcome and generated a data set containing 13,490 reactions for training specifically designed GNNbased machine learning models. The general screening procedure, including information on the hardware and software utilized, is provided in the SI (SI3).