Hydrochloric Acid → HCID 66712317, compound

Participants

Reaction Conditions

Reaction Steps

7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (1.00 g, 4.10 mmol), 2-aminophenylboronic acid pinocl ester (1.84 g, 8.40 mmol), and Tetrakis(triphenylphosphine)palladium(0) (0.710 g, 0.614 mmol) were dissolved in Ethanol (15 mL) and Tetrahydrofuran (15 mL) followed by addition of 2.00 M of Sodium carbonate in Water (5.0 mL, 10 mmol). The reaction mixture was then heated at 75° C. and was allowed to stir overnight. After cooling to room temperature, the reaction mixture was acidified with ˜2 mL concentrated HCl and then extracted with EtOAc (2×, 30 mL). The organics were then back extracted with 3M HCl (2×, 20 mL) and the aqueous layers combined and washed with EtOAc (2×, 20 mL). The combined HCl was then basified while stirring with 5N NaOH followed by extraction with DCM (3×, 30 mL) and brine, drying with sodium sulfate, and conc. in vacuo. The product was then purified by ISCO column chromatography (50/50 EtOAc/Hex, 40 g column) to afford 2-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenylamine as a white solid (0.78 g, 74%). LCMS: 257 (M+H). 1H-NMR (CDCl3): 8.74 (s, 1H), 7.44 (d, 1H, J=7.72 Hz), 6.98 (d, 1H, J=4.82 Hz), 6.94 (d, 1H, J=4.82 Hz), 6.88 (d, 1H, J=7.78 Hz), 6.84 (d, 1H, J=7.78 Hz), 4.12 (m, 2H), 2.50 (s, 3H).

Provenance & Evidence