TERT-BUTYL 3-BROMO-1H-PYRROLO[2,3-B]PYRIDINE-1-CARBOXYLATE Chemical Properties

Boiling point:

376.7±45.0 °C(Predicted)

Density 

1.46±0.1 g/cm3(Predicted)

storage temp. 

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

pka

1.65±0.30(Predicted)

Appearance

Light yellow to yellow Liquid

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933399990

TERT-BUTYL 3-BROMO-1H-PYRROLO[2,3-B]PYRIDINE-1-CARBOXYLATE Usage And Synthesis

Synthesis

Under nitrogen atmosphere, 3-bromo-1H-pyrrolo[2,3-b]pyridine (0.10 g, 0.50 mmol) was dissolved in tetrahydrofuran (THF, 4.0 mL) followed by the addition of 4-dimethylaminopyridine (DMAP, 0.006 g, 0.06 mmol). The reaction mixture was cooled to -20 °C and di-tert-butyl dicarbonate (Boc anhydride, 122 μL, 0.56 mmol) was slowly added. The reaction mixture was gradually warmed to room temperature and stirred continuously for 2 hours. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, water (20 mL) was added to the mixture and extracted with ethyl acetate (EtOAc, 3 × 50 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (60-120 mesh, 5% ethyl acetate-hexane as eluent) to afford the target product 1-BOC-3-bromo-7-azaindole as an oil (0.12 g, 79% yield).

References

[1] Synthesis, 1999, # 4, p. 615 - 620
[2] Patent: WO2009/74812, 2009, A1. Location in patent: Page/Page column 59

TERT-BUTYL 3-BROMO-1H-PYRROLO[2,3-B]PYRIDINE-1-CARBOXYLATE(226085-17-2)Related Product Information

• 1-METHYL-3-BROMO-7-AZAINDOLE
• 3-Bromo-7-azaindole
• 1-Boc-7-azaindole
• TERT-BUTYL 3-BROMO-1H-PYRROLO[2,3-B]PYRIDINE-1-CARBOXYLATE
• tert-butyl 3-broMo-6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxylate
• 1-Boc-3-bromo-6-methylindole
• 3-BROMOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 3-FORMYL-4-HYDROXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER