Triethylamine → 3-Amino-5-bromothiophene-2-carboxamide

A mixture of 3-amino-5-bromothiophene-2-carboxylic acid (0.154 g, 0.690 mmol), ammonium chloride (0.369 g, 6.90 mmol), triethylamine (0.964 mL, 6.90 mmol) and DMF (4.0 mL) was stirred for 10 min. Then, 1-hydroxybenzotriazole (0.284 g, 2.10 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.403 g, 2.10 mmol) were added and stirring was continued for 4 days. The mixture was then poured into sat. aqueous sodium hydrogen carbonate (100 mL). Extraction with ethyl acetate (60 mL, 20 mL), washing with brine, drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. This oil was purified by column chromatography (Combiflash, silica gel, hexanes to 90:10 hexanes/ethyl acetate) to afford the title compound (0.118 g, 78%) as a brown oil:

1. stirringstirring
2. waitwas continued for 4 days
3. extractionExtraction with ethyl acetate (60 mL, 20 mL)
4. washwashing with brine
5. dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
6. customgave an oil
7. customThis oil was purified by column chromatography (Combiflash, silica gel, hexanes to 90:10 hexanes/ethyl acetate)

ORD record

ord-3fe3b2d08394469a8981f5137ee9e269

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691828B2