Dimethylformamide → 1H-Indole-6-carboxaldehyde

Potassium hexamethyldisilazane (0.5M in toluene) (56 ml) was added dropwise to a ice cold solution of 6-bromoindole (5.0 g) in diethyl ether (50 ml). The reaction mixture was warmed to room temperature for 30 mins and then cooled to −78° C. tBuLi (1.7M) (31.5 ml) was added to the mixture keeping the temperature below −65° C. the mixture was further stirred at −78° C. for 30 mins after which time a solution of DMF (6 ml) in diethyl ether (10 ml) was added, the reaction mixture was warmed to room temperature and quenched with ice cold 2N HCl the product was then extracted into diethyl ether (×3). The combined organic layers were dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with Dichloromethane/Methanol (97/3, v/v) to afford the title compound as a solid (1.49 g).

1. additionwas added to the mixture
2. customthe temperature below −65° C.
3. additionwas added
4. temperaturethe reaction mixture was warmed to room temperature
5. customquenched with ice cold 2N HCl the product
6. extractionwas then extracted into diethyl ether (×3)
7. dry with materialThe combined organic layers were dried over MgSO4
8. customevaporated under reduced pressure
9. customThe crude product was purified by column chromatography on silica gel eluting with Dichloromethane/Methanol (97/3

ORD record

ord-3fc0d159b31c4499baab8e384cac9dc4

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06200978B1