Triisopropyl borate → HCID 55265943, compound

To a stirring mixture consisting of thieno[3,2-c]pyridine (2.0 g) in anhydrous tetrahydrofuran (25 mL) at −40° C. was added a solution consisting of 1.6 M n-butyllithium in hexanes (10 mL) over several minutes (dropwise at first followed by a slow, steady stream). The reaction mixture was stirred for five minutes and triisopropyl borate (4.2 mL) was subsequently added. The cold bath was removed and the mixture was allowed to stir for one hour. Water (2 mL) was added to the stirring mixture, which caused a pale yellow solid to precipitate instantly. The precipitate was collected by vacuum filtration and the solids were rinsed lightly with water (giving a cloudy yellow filtrate) and subsequently with diethyl ether (giving a dark orange filtrate). The aqueous portion of the filtrate was separated from the organic solvent, and then diluted with 1,4-dioxane (100 mL) and the solution was concentrated under reduced pressure. Addition of 1,4-dioxane (100 mL) to the concentrate and subsequent concentration under reduced pressure was repeated twice to afford a yellow powder (0.8 g) upon final evaporation.

1. additionwas added a solution
2. customThe cold bath was removed
3. stirringto stir for one hour
4. additionWater (2 mL) was added to the stirring mixture, which
5. customto precipitate instantly
6. filtrationThe precipitate was collected by vacuum filtration
7. washthe solids were rinsed lightly with water (
8. customgiving a cloudy yellow filtrate) and subsequently with diethyl ether (
9. customgiving a dark orange filtrate)
10. customThe aqueous portion of the filtrate was separated from the organic solvent
11. additiondiluted with 1,4-dioxane (100 mL)
12. concentrationthe solution was concentrated under reduced pressure
13. additionAddition of 1,4-dioxane (100 mL) to the
14. concentrationconcentrate
15. concentrationsubsequent concentration under reduced pressure

ORD record

ord-7a7674fcbf2a46c99d78cf36bd95786f

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260450B2