Reaction #1277441

Reaction equation

HATU

9-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid

ammonium chloride

DIEA

→

9-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide

Solvents

sodium bicarbonate

ethyl acetate

THF

Conditions

Workup

1. 1
   FiltrationThe mixture was filtered
2. 2
   Extractionthe filtrate was extracted with EtOAc
3. 3
   WashThe combined organic extracts were washed with water, brine
4. 4
   Dryingdried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure

Procedure

To 9-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2.13 g, 6.53 mmol) in THF (22 mL) was added ammonium chloride (1.40 g, 26.1 mmol), DIEA (2.27 mL, 13.1 mmol), and then HATU (2.73 g, 7.18 mmol). The reaction mixture was allowed to stir at room temperature for 16 h. The reaction mixture was diluted with sodium bicarbonate and ethyl acetate. The mixture was filtered and the filtrate was extracted with EtOAc. The combined organic extracts were washed with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give 9-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide (2.12, quantitative yield). LC/MS (ESI+): m/z 327 (M+H)

Source