Water → HCID 22614254, compound

Temperature

0 °C

Sodium hydride (60 %wt suspension in mineral oil; 0.86 g, 21.5 mmol) is suspended in dry tetrahydrofuran (THF, 20 mL) and is cooled to 0° C. A mixture of 4-chloroindole (2.5 g, 16.5 mmol) and THF (10 mL) is added to the slurry at 4° C. After the addition is completed, the mixture is stirred for 30 min. Then a mixture of O-mesitylenesulfonylhydroxylamine (3.02 g, 14 mmol) and THF (25 mL) is added slowly at a temperature below 5° C. After the addition is completed, the reaction mixture is allowed to reach room temperature and is subsequently stirred for 3 h. Then the mixture is cooled again to 0° C., and a second aliquot of O-mesitylenesulfonylhydroxylamine (3.02 g, 14 mmol) in THF (25 mL) is added slowly. The mixture is allowed to reach ambient temperature and was subsequently stirred overnight. The reaction mixture is worked up by adding it to water, extracting into ethyl acetate, and drying over sodium sulfate. The crude product (4 g) is obtained after filtration of the drying agent and evaporation of the solvent. The aminated indole (2,2 g) is obtained as a black oil (mixture of starting material and product) after flash chromatography, using toluene as eluent.

1. additionis added to the slurry at 4° C
2. additionAfter the addition
3. additionis added slowly at a temperature below 5° C
4. additionAfter the addition
5. customto reach room temperature
6. stirringis subsequently stirred for 3 h
7. temperatureThen the mixture is cooled again to 0° C.
8. customto reach ambient temperature
9. waitwas subsequently stirred overnight
10. extractionextracting into ethyl acetate
11. dry with materialdrying over sodium sulfate
12. customThe crude product (4 g) is obtained
13. filtrationafter filtration of the drying agent and evaporation of the solvent

ORD record

ord-cf503f6e049c46d491b00b4e53df5555

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06376426B1