tert-butyl 6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

tert-butyl 6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate Property

Boiling point:

339.1±42.0 °C(Predicted)

Density 

1.173

storage temp. 

2-8°C(protect from light)

pka

-1.51±0.20(Predicted)

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

tert-butyl 6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of tert-butyl 6,7-dihydrothieno[3,2-C]pyridine-5(4H)-carboxylate from 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (5 g, 28.46 mmol) and di-tert-butyl dicarbonate (6.83 g, 31.30 mmol) is as follows: 4,5,6,7-tetrahydrothieno[3,2-c] pyridine hydrochloride was suspended in 150 mL of dichloromethane, triethylamine (3.17 g, 31.30 mmol) was added followed by slow addition of solid di-tert-butyl dicarbonate. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the organic phase was washed sequentially with water (2 x 100 mL) and brine (2 x 100 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give a colorless oily product (6.8 g, 100% yield), which solidified to a white solid on standing.

References

[1] Patent: WO2009/49028, 2009, A1. Location in patent: Page/Page column 156
[2] Patent: CN104497008, 2016, B. Location in patent: Paragraph 0190; 0192; 0193
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3687 - 3706
[4] Patent: CN104341433, 2017, B. Location in patent: Paragraph 0036; 0037