Hydrazine → HCID 53258711, compound

Participants

Reaction Steps

To a solution of tert-butyl 3-(1-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-methoxy-2-methyl-1,3-dioxopropan-2-yl)-1H-indole-1-carboxylate (6) (0.26 g, 0.52 mmol) in glacial acetic acid (2 mL) was added hydrazine (35% in H2O, 0.25 mL) followed by a catalytic amount of camphor sulfonic acid (10 mg). The reaction mixture was then microwaved at 210° C. for 10 hours. The solvent was then removed under reduced pressure and the residue partitioned between dichloromethane (10 mL) and aqueous Na2CO3 (20 mL). The organic layer was separated, dried using Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by reverse phase (HPLC, C-18) chromatography using trifluoroacetic acid as a modifier to give the desired product (7) (0.033 g, 17% yield) as a white solid. 400 MHz 1H NMR (CDCl3) δ: 11.44 (s, 1H), 11.18 (s, 1H), 7.91 (d, J=4.2 Hz, 1h), 7.6 (d, J=1.4 Hz, 1H), 7.37-7.28 (m, 2H), 7.15-7.1 (m, 1H), 7.08-6.96 (m, 2H), 6.95-6.88 (m, 1H), 6.82 (t, J=6.8 Hz, 1H), 4.08-3.88 (m, 2H), 2.9-2.78 (m, 2H), 2.08-1.96 (m, 2H), 1.82 (s, 3H); LCMS [M+H]: 369.

Provenance & Evidence