Benzylamine → HCID 76852922, compound

Participants

Reaction Steps

7-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (Example 138) (102 mg, 0.565 mmol) was dissolved in methanol (2.5 mL). Benzylamine (70 μL, 0.62 mmol) was added. After 2 h, sodium borohydride (35 mg, 0.90 mmol) was added. After an additional 2 h, the reaction mixture was quenched by addition of 59% aqueous sodium bicarbonate. The reaction mixture was extracted with diethyl ether, dried (magnesium sulfate), and evaporated to dryness (124 mg, 81% crude). The crude material was dissolved in acetonitrile and treated with hydrochloric acid (0.46 mL, 1 M in diethyl ether) to give N-benzyl-N-[(7-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)methyl]amine hydrochloride (107 mg, 0.347 mmol, 61%) as an off-white powder: mp 201-204° C.; 1H NMR (300 MHz, CD3OD) δ4.35 (2H, s), 4.52 (2H, s), 6.87 (1H, s), 7.45-7.60 (5H, m), 7.60 (1H, d, J=5.6 Hz), 7.94 (1H, d, J=5.6 Hz); ESI MS m/z 272 [C15H14ClN3+H]+; HPLC (H2O/CH3CN 90:10 to 0:100 over 20 min, hold for 15 min, 0.05% TFA added to solvents) >99%, tR=11.1 min.

Provenance & Evidence