5-Methylindolin-2-one → HCID 178422516, compound

Participants

Reaction Steps

The title compound was synthesized according to the method described in Example A57 from 5-methylindolin-2-one (8.0 mg, 0.0535 mmol) and (E)-N-(2-(dimethylamino)ethyl)-3-(6-formyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-yl)-N-methylacrylamide (23 mg, 0.0535 mmol) with a modified purification procedure. The product was extracted into EtOAc after the final deprotection step and washed with NaHCO3(sat) (2×), brine (2×) and the organic layer dried over MgSO4. After removal of solvent the resulting film was titurated with Et2O/hexanes to give after drying 9.4 mg, 41% yield of a yellow solid which was a 77:23 mixture of (E)/(Z) isomers. 1H NMR (400 MHz, CD3OD) δ 8.94, 7.91 (s, 1H), 8.20, 8.16 (d, J=8.7 Hz, 1H), 7.98-7.93 (m, 1H), 7.84 (s, 1H), 7.59, 7.43 (d, J=8.2 Hz, 1H), 7.52-7.42 (m, 2H), 7.08 (d, J=7.2 Hz, 1H), 6.82, 6.78 (d, J=7.6 Hz, 1H), 3.77-3.68 (m, 2H), 3.60, 3.13 (s, 3H), 2.68-2.61 (m, 2H), 2.37 (s, 6H), 2.19 (s, 3H); MS ESI 430.3 [M+H]+, calcd for [C25H27N5O2+H]+ 430.22.

Provenance & Evidence