Triethylamine → HCID 57845129, compound

To a solution of (E)-3-(4-bromothiophen-2-yl)acrylic acid (9.30 g, 39.9 mmol) in acetone (100 mL), triethylamine (4.24 g, 41.9 mmol) was added under nitrogen atmosphere. At 0° C., isobutyl chloroformiate (5.72 g, 41.9 mmol) was slowly added and then, the mixture was stirred for 1 h. 4.67 g (71.8 mmol) of sodium azide dissolved in 10 mL of water was slowly added at 0° C., the mixture was stirred at 0° C. for a further hour and then warmed up to room temperature overnight. The reaction mixture was extracted with EA/water. The organic phase was washed aq. NaHCO3 solution and then with brine. The organic phase was dried over MgSO4, concentrated to dryness and the residue was purified by trituration with diisopropyl ether to afford a bright beige solid (9.00 g, 34.9 mmol). Yield: 87%.

1. additionAt 0° C., isobutyl chloroformiate (5.72 g, 41.9 mmol) was slowly added
2. additionwas slowly added at 0° C.
3. stirringthe mixture was stirred at 0° C. for a further hour
4. extractionThe reaction mixture was extracted with EA/water
5. washThe organic phase was washed aq. NaHCO3 solution
6. dry with materialThe organic phase was dried over MgSO4
7. concentrationconcentrated to dryness
8. customthe residue was purified by trituration with diisopropyl ether

ORD record

ord-89655e60eb454932b409a032220900c9

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273068B2