Indole → HCID 4389257, compound

The title compound was prepared according to general procedure A described in Scheme 1. A solution of indole (5 g, 43 mmol) in DMF (60 mL) at to 0° C. was treated with NaH (60% in mineral oil, 3.4 g, 86 mmol) in 4 portions providing a slurry that was gradually warmed to RT over a 30 min period. Isopropyl iodide (1.1 g, 64 mmol) was added to the reaction mixture at RT and the mixture was stirred for 14 h. The reaction mixture was then treated with H2O (50 mL) and extracted with EtOAc (3×50 mL). The combined organic extracts were washed with sat. NaHCO3 (1×50 mL), H2O (1×50 mL) and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the crude material was purified on silica gel (Biotage, 0-10% EtOAc/Hexanes, 30 min.) to provide N-isopropylindole as a colorless oil (2.9 g, 43% yield).

1. customThe title compound was prepared
2. customproviding a slurry that
3. extractionextracted with EtOAc (3×50 mL)
4. washThe combined organic extracts were washed with sat. NaHCO3 (1×50 mL), H2O (1×50 mL)
5. dry with materialdried over anhydrous Na2SO4
6. customThe solvent was removed under reduced pressure
7. customthe crude material was purified on silica gel (Biotage, 0-10% EtOAc/Hexanes, 30 min.)

ORD record

ord-f180e6e04df043ce949c80633a048c5a

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08114894B2