Hydrochloric Acid → HCID 10172423, compound

Participants

Reaction Conditions

Reaction Steps

1,3,3-Trimethylindoline-6-ylamine. A solution of 3,3-dimethyl-6-nitroindoline, Example 32(a), (0.23 g, 1.2 mmol) in anhydrous DMF (15 mL) was magnetically stirred at 25° C. and treated with sodium hydride (0.14 g, 3.6 mmol, 60% dispersion in mineral oil, Aldrich), followed by iodomethane (0.17, 1.3 mmol, Aldrich). The reaction mixture was stirred at 25° C. for 3 h, then quenched with water (40 mL) and extracted with EtOAc (3×30 mL). The combined extract was concentrated in vacuo to provide a residue [MS (ESI, pos. ion) m/z: 207 (M+1)] which was immediately dissolved in ethyl ether (5 mL), magnetically stirred at 0° C., and treated with tin (II) chloride dihydrate (1.7 g, 7.5 mmol, Aldrich) and cond HCl (0.8 mL). The reaction mixture was stirred at 0° C. for 10 min, allowed to warm to 25° C., then stirred at that temperature overnight. The reaction mixture was washed with 10 N NaOH (20 mL) and extracted with EtOAc (3×50 mL). The combined extracts were concentrated in vacuo and purified by silica gel chromatography to provide the title product. MS (ESI, pos. ion) m/z: 177 (M+1).

Provenance & Evidence