Ammonia → HCID 86757913, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-(1H-pyrrolo[2,3-f]quinolin-1-yl)-2-propylamine (0.025 g, 0.11 mmol), 3,4-methylenedioxybenzaldehyde (0.033 g, 0.22 mmol) and methanol (1 mL) was shaken for 3 h. To the mixture was added Amberlite IRA-400 borohydride resin (2.5 mmol/g —BH4, 0.12 g, 0.3 mmol) and the mixture was shaken for 18 h. To the mixture was added PS-benzaldehyde (2.5 mmol/g —CHO, 0.12 g, 0.3 mmol) and the mixture was shaken for 18 h and filtered. The filter-cake was washed with dichloromethane (2×1 mL) and methanol (2×1 mL) and the filtrate was concentrated in vacuo. The concentrate was dissolved in dichloromethane (2 mL) and Amberlyst-15 (0.5 g) was added. The mixture was shaken for 1 h and filtered. The filter-cake was washed with dichloromethane (2×1 mL) and methanol (2×1 mL), suspended in methanolic ammonia solution (2 M, 1 ML, 2 mmol), shaken for 1 h, and filtered. The filter-cake was washed (dichloromethane) and the filtrate was concentrated in vacuo, treated with a solution of fumaric acid (0.030 g, 0.26 mmol) in 2-propanol (2 mL), cooled to 0° C., shaken for 1 h and filtered. The filter-cake was dried to give the product as a beige solid (0.052 g, 79%): mp 171-175° C. (dec); NMR ΔH (400 MHz, DMSO-d6) 0.99 (3H, d, J 6.5 Hz) 3.15 (1H, m) 3.58 (1H, d, J 14 Hz) 3.73 (1H, d, J 14 Hz) 4.46 (1H, dd, J 8.5, 14.5 Hz) 4.76 (1H, dd, J 6, 14.5 Hz) 5.96 (2H, s) 6.66 (1H, d, J 7.5 Hz) 6.73 (1H, d, J 7.5 Hz) 6.87 (1H, s) 7.47 (1H, dd, J 4.5, 8.5 Hz) 7.50 (1H, d, J 3 Hz) 7.64 (1H, d, J 9 Hz) 7.94 (1H, d, J 9 Hz) 8.64 (1H, d, J 8.5 Hz) 8.77 (1H, d, J 4 Hz).

Provenance & Evidence