Formaldehyde → HCID 69060576, compound

Participants

Reaction Steps

To a solution of (S,S)-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-(1H-indol-2-yl)-methanone hydrochloride (50 mg, 0.18 mmol), TEA (50 μL, 0.36 mmol), and formaldehyde (6 μL, 0.22 mmol) in dichloroethane (DCE)/MeOH (10:1, 3 mL) was added NaB(OAc)3H (115 mg, 0.54 mmol). After 2 h at rt, the mixture was diluted with satd. aq. NaHCO3 and extracted with CH2Cl2 (3×). The combined organic layers were washed with satd aq. NaCl, dried (Na2SO4), and concentrated to yield an orange solid (44 mg, 96%). MS (ESI): mass calcd. for C15H17N3O, 255.14; m/z found, 256.4 [M+H]+. 1H NMR (mixture of rotamers; CDCl3): 10.34-10.08 (m, 1H), 7.64-7.54 (m, 1H), 7.44-7.35 (m, 1H), 7.24-7.16 (m, 1H), 7.09-7.00 (m, 1H), 6.80 (s, 0.5H), 6.67 (s, 0.5H), 4.99-4.86 (m, 1H), 4.05-3.95 (m, 0.7H), 3.84-3.77 (m, 0.3H), 3.71-3.62 (m, 1H), 3.55-3.46 (m, 1H), 3.18-3.10 (m, 0.3H), 2.98-2.88 (m, 0.7H), 2.82-2.69 (m, 1H), 2.46-2.31 (m, 3H), 1.98-1.88 (m, 1H), 1.79-1.70 (m, 1H).

Provenance & Evidence