Sodium Hydroxide → HCID 86698782, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of crude 1-tert-butyl 3-methyl 6-chloro-5-[4-(pyridin-3-ylmethoxy)phenyl]-1H-indole-1,3-dicarboxylate (37 mg, 0.075 mmol), methanol (0.8 mL) and 1M aqueous sodium hydroxide (0.45 mL, 0.45 mmol) was sealed in a vial and heated at 75° C. for 17 hours, causing a solution to form. After cooling to room temperature, the reaction mixture was concentrated via a stream of nitrogen, and diluted with ethyl acetate and saturated aqueous citric acid slowly. The layers were separated, and the aqueous layer was extracted two times with ethyl acetate. The organic layers were combined, concentrated in vacuo, and the resulting clear oil was dissolved in DMSO (0.9 mL) and purified via reverse phase prep-HPLC to give the title compound (6.4 mg, 23% over two steps). MS (ES+) 379.1 (M+H)+. Retention time: 2.28 min. Column: Waters Atlantis dC18 4.6×50 mm, 5 μm. Modifier: TFA 0.05%. Gradient: 95% H2O/5% MeCN linear to 5% H2O/95% MeCN over 4.0 min, HOLD at 5% H2O/95% MeCN to 5.0 min. Flow: 2.0 mL/min.

Provenance & Evidence