1-[(1S)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinone → 5-Chloro-3-(7-chloro-5-methoxy-2,3-dihydro-1H-indol-1-yl)-1-[(1S)-1-cyclopropylpropyl]-2(1H)-pyrazinone

Participants

Reaction Steps

Prepared in a similar fashion as described for Example 413 using 3,5-dichloro-1-[(1S)-1-cyclopropylpropyl]-2(1H)-pyrazinone and 7-chloro-5-methoxyindoline hydrochloride as the starting materials. mp 128–130° C.; 1H NMR (300 MHz, CDCl3): δ 6.93 (s, 1 H), 6.71 (s, 2 H), 4.34–4.24 (m, 2 H), 4.11–3.99 (m, 1 H), 3.75 (s, 3 H), 3.08 (t, J=7.9 Hz, 2 H), 1.93–1.73 (m, 2 H), 1.06–0.99 (m, 1 H), 0.92 (t, J=7.3 Hz, 3 H), 0.79–0.72 (m, 1 H), 0.54–0.43 (m, 2 H), 0.34–0.24 (m, 1 H); HRMS (ESI) calcd for C19H22N3O2Cl2 (M+H)+: 394.1089; found m/z 394.1088.

Provenance & Evidence