Dimethylformamide → HCID 66760607, compound

To a cooled (0° C.) mixture of 3-bromothieno[2,3-c]pyridine-2-carboxylic acid (50 mg, 0.19 mmol), DCM (1 mL) and DMF (10 μL, 0.1 mmol) was added oxalyl chloride (29 μL, 0.34 mmol). The ice bath was removed and the mixture was stirred at room temperature for 1 h. Oxalyl chloride (29 μL, 0.34 mmol) was added again and the mixture was stirred at room temperature for 1 h. The solvent was evaporated and THF (1 mL) was added. Ammonium hydroxide (0.7 mL, 20 mmol) was added to the mixture and stirred at room temperature for 1 h. The precipitate was filtered and washed with DCM and used without further purification. 1H NMR (400 MHz, CD3OD): δ 9.20-9.27 (m, 1 H), 8.61 (d, J=5.8 Hz, 1 H), 7.89 (dd, J=5.7, 0.9 Hz, 1 H); MS (ESI): 257.33, 259.35 [M+H]+; HPLC tR=0.52 min (HPLC: Analytical—2 min).

1. temperatureTo a cooled
2. customThe ice bath was removed
3. stirringthe mixture was stirred at room temperature for 1 h
4. customThe solvent was evaporated
5. additionTHF (1 mL) was added
6. stirringstirred at room temperature for 1 h
7. filtrationThe precipitate was filtered
8. washwashed with DCM
9. customused without further purification
10. customHPLC tR=0.52 min (HPLC: Analytical—2 min)

ORD record

ord-125ed991675a4f1481087c741cc16d76

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08378104B2