Dichloromethane → Ammonia dichloromethane

Participants

Reaction Steps

A solution of the product of Example 9 (0.51 g), 2-aminopyridine (0.24 g), and acetic acid (0.12 mL) in DCM (7 mL) was treated with sodium triacetoxyborohydride (650 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (10 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1-4% 2 M methanolic ammonia/DCM) gave the title compound as an off white solid (440 mg). 1H NMR (400 MHz, CDCl3): 8.05 (m, 1H), 7.35 (m, 1H), 7.23 (d, J=8.6 Hz, 2H), 6.83 (d, J=8.6 Hz, 2H), 6.53 (m, 1H), 6.32 (m, 1H), 5.05 (m, 1H), 4.37 (d, J=5.6, 2H), 3.95 (t, J=6.3 Hz, 2H), 2.44 (m, 2H), 2.37 (br, 4H), 1.94 (m, 2H), 1.59-1.53 (m, 4H), 1.45-1.38 (m, 2H).

Provenance & Evidence