Oxindole → HCID 69659194, compound

To a solution of oxindole (1.10 g, 8.27 mmol) in dimethoxyethane (30.0 ml) at room temperature was added 1.0M LiHMDS/THF (17.0 ml). The mixture was stirred for 10 minutes at room temperature, and lithium 3-oxo-1,3-dihydro-2-benzofuran-1-carboxylate (1.37 g, 7.44 mmol) was added in one portion. After the reaction was rapidly stirred at room temperature for 18 hours, it was quenched into 4% HCl aqueous solution (200 mL), and the mixture was stirred 5 minutes. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water and then extracted with saturated NaHCO3 aqueous solution. The aqueous layer was acidified with 4% HCl aqueous solution, and extracted with EtOAc. The combined organic layers were washed with brine, dried with anhydrous Na2SO4, and rotary evaporated to obtain a yellow solid. The yellow solid was triturated at room temperature with CHCl3, and then triturated with hot isopropanol to give 3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-carboxylic acid as a yellow solid (287 mg, 13%).

1. stirringAfter the reaction was rapidly stirred at room temperature for 18 hours
2. customit was quenched into 4% HCl aqueous solution (200 mL)
3. stirringthe mixture was stirred 5 minutes
4. extractionThe aqueous layer was extracted with EtOAc
5. washThe combined organic layers were washed with water
6. extractionextracted with saturated NaHCO3 aqueous solution
7. extractionextracted with EtOAc
8. washThe combined organic layers were washed with brine
9. dry with materialdried with anhydrous Na2SO4
10. customrotary evaporated
11. customto obtain a yellow solid
12. customThe yellow solid was triturated at room temperature with CHCl3
13. customtriturated with hot isopropanol

ORD record

ord-a137625f4294466aa8ea4c9a91d97b29

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07060844B2