(3S)-(-)-3-(Dimethylamino)pyrrolidine → (S)-1-(4-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)benzyl)-N,N-dimethylpyrrolidin-3-amine

Participants

Reaction Steps

To a suspension of 52 (1.0 g, 2.41 mmol) in DME (˜20 ml) was added (S)—N,N-dimethylpyrrolidin-3-amine (413 mg, 3.62 mmol) and TEA (486 mg, 2 eq, 4.82 mmol) and the reaction mixture was heated to reflux for an hour. The reaction mixture was cooled to RT, filtered then concentrated. The mixture was partitioned between EtOAc/H2O and the biphasic system was filtered and the resultant yellow solid was collected was collected by filtration to afford title compound 60 (450 mg, 38% yield). The organic phase was separated from the biphasic system; it was then dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (9:1 EtOAc:MeOH+1% conc NH4OH solution) to afford an additional amount of 60 (82 mg, 7% yield). MS (m/z): 493 (M+H).

Provenance & Evidence