Pd-catalysed Buchwald-Hartwig C-N cross-coupling reactions from a high throughput ex-periment by Ahneman et al. . For this data set, 11 splits were defined; seven splits where the relative size of the training set was decreased from 70 to 2.5% and four out-of-sample splits based on isoxazole additives. DRFP performs better on the random splits than the DFT-based fingerprint with random forests and Yield-BERT but is outperformed by the augmented Yield-BERT by a narrow margin. In the out-of-sample splits, DRFP performs better than the augmented version of Yield-BERT and the DFT-based method, yet the nonaugmented Yield-BERT performs slightly better. When averaging over all 11 tests, DRFP performs best. The performance of DRFP was further tested on a data set containing Suzuki-Miyaura reactions and the USPTO reaction data set. In both cases, DRFP performed better than Yield-BERT. However, similar to the Buchwald-Hartwig reaction data, the difference between the two approaches is relatively small. Both methods perform better on reactions with a sub-gram scale yield.