Methanol → HCID 21107343, compound

Temperature

200 °C

To a solution of 3-bromo-9H-carbazole (4.00 g, 16.3 mmol, 1 equiv) in N-Methyl-2-pyrrolidinone (40 mL) was added copper(I) cyanide (1.6012 g, 17.9 mmol, 1.1 equiv). The mixture was sealed and heated at 200° C. until TLC showed no starting material. The reaction solution was cooled and 60 mL of water was added. The off-white precipitate was filtered off and washed with EtOAc (3×20 mL). This filtrate was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with water (20 mL) and brine (20 mL), and then dried over Na2SO4. The solvent was removed under reduced pressure to afford red-brown oil. Methanol was added to the crude oil to afford 0.8251 g off-white precipitate as pure product. The mother liquid from the methanol precipitation was concentrated and purified by chromatography (25% EtOAc/Hex) to provide 0.28 g off-white solid. The combined yield was 35.5%.

1. customThe mixture was sealed
2. temperatureThe reaction solution was cooled
3. filtrationThe off-white precipitate was filtered off
4. washwashed with EtOAc (3×20 mL)
5. extractionThis filtrate was extracted with ethyl acetate (3×20 mL)
6. washThe combined organic layers were washed with water (20 mL) and brine (20 mL)
7. dry with materialdried over Na2SO4
8. customThe solvent was removed under reduced pressure
9. customto afford red-brown oil

ORD record

ord-9823f1f35c8a4cc3931db54972aac46a

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735440B2