Novel Methoxymethyl 3‐Bromoboldine Derivatives with Improved Capabilities as Precursors for Organic Synthesis

Abstract Ortho‐directed metalation of boldine (1) is a possible route to new compounds with pharmacological potential. Three new methoxymethyl (MOM) derivatives of 3‐bromoboldine were prepared and fully characterized: 2‐O‐methoxymethyl‐3‐bromoboldine (5), 9‐O‐methoxymethyl‐3‐bromoboldine (6), and 2,9‐O,O′‐dimethoxymethyl‐3‐bromoboldine (7). Compound (7) proved to be superior in yield and selectivity to 2,9‐ O,O′‐dimethoxymethylboldine (3) as a reaction precursor for the preparation of novel 3‐substituted boldine derivatives.