2-BROMO-5,6-DIHYDROTHIENO[2,3-C]PYRIDIN-7(4H)-ONE

2-BROMO-5,6-DIHYDROTHIENO[2,3-C]PYRIDIN-7(4H)-ONE Property

Boiling point:

471.8±45.0 °C(Predicted)

Density 

1.726±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

13.97±0.20(Predicted)

Appearance

White to off-white Solid

Safety

HS Code 

2934999090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

2-BROMO-5,6-DIHYDROTHIENO[2,3-C]PYRIDIN-7(4H)-ONE Chemical Properties,Usage,Production

Uses

2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one is an intermediate in preparation of thieno[2,3-c]pyridine derivatives as MCH receptor antagonists.

Synthesis

General procedure for the synthesis of 2-bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-ones from 5,6-dihydrothieno[2,3-c]pyridin-7(4H)-ones: 5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (4.80 g, 31.37 mmol) was dissolved in acetic acid (40 mL) and water (30 mL ) in a solvent mixture. After cooling the reaction mixture to 0°C, bromine (1.8 mL, 34.51 mmol) was added slowly and dropwise. The reaction was continuously stirred at 0°C for 1 hour. After completion of the reaction, the reaction mixture was diluted with 100 mL of water and extracted with ethyl acetate (3 x 100 mL). The organic layers were combined, washed sequentially with 5% sodium sulfite solution (2 × 50 mL) and saturated sodium bicarbonate solution (2 × 100 mL), dried over anhydrous sodium sulfate, filtered and concentrated to afford 6.20 g (85% yield) of the target product 2-bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one. Mass spectral analysis (MS/ESI) m/z (81Br) 233.9 [M+H]+.

References

[1] Patent: WO2007/146759, 2007, A2. Location in patent: Page/Page column 26
[2] Patent: WO2007/146758, 2007, A2. Location in patent: Page/Page column 34
[3] Patent: US2012/225857, 2012, A1. Location in patent: Page/Page column 16