Water → 1H-Indole-2-carboxamide

To a solution of substituted indole-2-carboxylic acid (1e: 1 mmol) in dry DMF (4 mL) were added HATU (1.5 eq.) and the desired amine (R6—NH2: 1.2 eq.) followed by DIPEA (5.0 eq.) at 0° C. The resulting mixture was stirred at room temperature for 12 h to 24 h. To the reaction mixture water (10 mL) was added and stirred for 10 minutes. The resultant solid was collected by filtration, washed with water, hexane and dried. In some instances reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude compounds were purified by column chromatography over silica gel (100-200 mesh) or CombiFlash® purification system (Teledyne Isco) using appropriate mixtures of ethyl acetate and hexanes/petroleum ether or preparative HPLC to obtain the desired product indole-2-carboxamide (I).

1. stirringstirred for 10 minutes
2. filtrationThe resultant solid was collected by filtration
3. washwashed with water, hexane
4. customdried
5. customIn some instances reaction mixture
6. extractionwas extracted with ethyl acetate
7. washThe organic layer was washed with water, brine
8. dry with materialdried over anhydrous Na2SO4
9. concentrationconcentrated under reduced pressure
10. customThe crude compounds were purified by column chromatography over silica gel (100-200 mesh) or CombiFlash® purification system (Teledyne Isco)

ORD record

ord-7ef158f6c6f34d80963be8687ce81787

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447039B2