637774-61-9 → HCID 59238928, compound

To a solution of diethyl 6-methoxy-5,7-dihydroindolo[2,3-b]carbazole-2,10-dicarboxylate (1.72 g, 4 mmol) in THF (40 mL), with stirring at 0-5° C. and under Ar, was slowly added a solution of LAH in THF (16 mL, 1.0 M). After addition of LAH solution, the mixture was warmed to room temperature and then refluxed 2 h. The reaction mixture was cooled in an ice-water bath and quenched by carefully adding ethyl acetate (20 mL) and water (20 mL). The resultant mixture was extracted with ethyl acetate (3×100 ml); the extracts were combined, washed with brine, dried over Na2SO4, filtered, and evaporated to dryness. The residue was subjected to chromatography on silica gel to give 6-methoxy-2,10-dimethyl-5,7-dihydroindolo[2,3-b]carbazole (180 mg, 14%), 1H NMR (400 MHz, DMSO-d6) δ ppm 10.97 (s, 2H), 8.45 (s, 1H), 7.91 (s, 2H), 7.33 (d, J=8.0 Hz, 2H), 7.14 (dd, J=1.2, 8.0 Hz, 2H), 4.07 (s, 3H), 2.49 (s, 6H).

1. temperaturerefluxed 2 h
2. temperatureThe reaction mixture was cooled in an ice-water bath
3. customquenched by carefully adding ethyl acetate (20 mL) and water (20 mL)
4. extractionThe resultant mixture was extracted with ethyl acetate (3×100 ml)
5. washwashed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customevaporated to dryness

ORD record

ord-6e185da06b624f0cbe8cecbdc59db958

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399502B2