Formaldehyde → HCID 10278717, compound

Participants

Reaction Steps

To N-(3,3-dimethyl-1-piperidin-4-ylmethyl-2,3-dihydro-1H-indol-6-yl)-2-(4-fluoro-benzylamino)-nicotinamide (0.92 g) dissolved in DCE (20 mL) at RT was added formaldehyde (37% aqueous, 0.42 mL) followed by NaBH(OAc)3 (1.59 g). After 4 h, the mixture was quenched with 1 N HCl (20 mL) and H2O (20 mL). It was basified with sat NaHCO3, extracted with CH2Cl2 (3×50 mL) and the combined extracts were washed with brine, dried (K2CO3) and concentrated onto SiO2 (previously treated with 10% MeOH (2 M NH3 in MeOH/CH2Cl2 and then concentrated in vacuo). The residue was purified by flash chromatography (Isco, 35 g column, 1-7% MeOH (2M NH3 in MeOH/CH2Cl2). The bulk of the crude yellow material was further purified by reverse phase Prep HPLC. The isolated fractions were partially concentrated and basified with 1 N NaOH and dried under vacuum to afford a slightly yellow powder. M+H=502.3. Calc'd for C30H36FN5O: 501.29.

Provenance & Evidence