Hydrochloric Acid → HCID 68496119, compound

5-(5-Nitropyridin-2-yloxy)-1H-indole (3.00 g, 11.8 mmol) was dissolved in 1,4-dioxane (30 mL). To the solution were added boran-trimethylamine complex (3.43 g, 47.0 mmol) and hydrochloric acid (1.96 mL, 23.5 mmol) and the resulting solution was refluxed for 1 hour. After cooling for 30 minutes, 6 M hydrochloric acid (9.40 mL, 56.4 mmol) was added to the solution, and the mixture was refluxed again. Thirty minutes later, the reaction mixture was cooled with ice and the pH of the solution was adjusted to 8 by dropwise addition of concentrated aqueous sodium hydroxide. Water (150 mL) was added to the solution, and the mixture was extracted with ethyl acetate (150 mL). After the organic layer was washed with brine, then dried over anhydrous sodium sulfate, the solvent was evaporated to yield 2.82 g of the title compound as reddish orange oil.

1. temperaturethe resulting solution was refluxed for 1 hour
2. temperatureAfter cooling for 30 minutes
3. temperaturethe mixture was refluxed again
4. temperatureThirty minutes later, the reaction mixture was cooled with ice
5. extractionthe mixture was extracted with ethyl acetate (150 mL)
6. washAfter the organic layer was washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. customthe solvent was evaporated

ORD record

ord-e0b2072d2b79430195fc97f3818aeb74

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08551999B2