Hydrochloric Acid → HCID 67314182, compound

A solution of 5-fluoro-1,3-dihydro-indol-2-one (110 mg, 0.72 mmol) in THF (5 mL) is treated with a solution of lithium bis(trimethylsilyl)amide (1.8 mL of a 1M solution in THF, 1.8 mmol) dropwise. The resulting solution is stirred at room temperature for 10 min. A solution of 2-(5-Hydroxy-piperidin-2-ylmethyl)-7H-furo[3,4-b]pyridin-5-one (90 mg, 0.36 mmol) in THF (2.5 mL) is added dropwise to the reaction mixture. The resulting solution is stirred for 4 h and is poured into a cold 4 M HCl solution in dioxane (4.5 mL) at 0° C. The resulting mixture is stirred at room temperature overnight. The reaction mixture is concentrated to partially remove the dioxane and is then partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organic phase is collected and the aqueous phase is extracted with additional EtOAc. The combined organic extracts are dried (Na2SO4), filtered and concentrated. The residue is purified by chromatography (silica gel) MeOH-Chloroform). The product containing fractions are concentrated to give the title compound as a yellow solid (41 mg, 30%).

1. stirringThe resulting solution is stirred for 4 h
2. stirringThe resulting mixture is stirred at room temperature overnight
3. concentrationThe reaction mixture is concentrated
4. customto partially remove the dioxane
5. customis then partitioned between EtOAc and saturated aqueous NaHCO3 solution
6. customThe organic phase is collected
7. extractionthe aqueous phase is extracted with additional EtOAc
8. dry with materialThe combined organic extracts are dried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue is purified by chromatography (silica gel) MeOH-Chloroform)
12. additionThe product containing fractions
13. concentrationare concentrated

ORD record

ord-0deac0c8ad0a4ca285bdcd727cfc8bf5

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455535B2