1H-PYRROLO[2,3-C]PYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER

1H-PYRROLO[2,3-C]PYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER Property

Melting point:

207-208 °C

Boiling point:

371.8±22.0 °C(Predicted)

Density 

1.272±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

12.67±0.40(Predicted)

Appearance

White to off-white Solid

Safety

HS Code 

2933998090

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.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

1H-PYRROLO[2,3-C]PYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER Chemical Properties,Usage,Production

Uses

Ethyl 1H-pyrrolo[2,3-c]pyridine-2-carboxylate is a useful research chemical.

Synthesis

1. tert-Butyl (4-methylpyridin-3-yl)carbamate (3.5 g, 16.8 mmol) was dissolved in anhydrous THF (30 ml) and cooled to -40 °C under argon protection. 2. tert-butyl lithium (20.7 ml, 1.7 M pentane solution, 35.2 mmol) was added slowly and the reaction mixture was kept stirred at -40 °C for 1 hour. 3. A solution of diethyl oxalate (2.5 ml, 18.5 mmol) in THF (30 ml) was added dropwise over 15 min. 4. the reaction mixture was warmed to 0 °C and stirring was continued for 2 h. The reaction mixture was then slowly warmed to room temperature and stirred for 19 h. The reaction mixture was then stirred for 1 h. The reaction mixture was then slowly warmed to room temperature. 5. 2N HCl (110 ml) was carefully added to the reaction mixture and heated to reflux for 2 hours. 6. After cooling, the organic phase was extracted by adding dichloromethane (100 ml) and the aqueous phase pH was adjusted to 8 and the organic phase was separated. 7. The aqueous phase was washed with dichloromethane (2 x 50 ml), the organic layers were combined, dried with magnesium sulfate and concentrated to give a light brown solid. 8. The solid was ground with ethyl acetate and the beige solid product (586 mg, 18%) was collected by filtration. LCMS (Method B): RT = 1.89min, M + H + = 190.

References

[1] Patent: US2010/216768, 2010, A1. Location in patent: Page/Page column 16-17