1H-Pyrrolo[2,3-b]pyridine, 4-chloro-2-iodo- Chemical Properties

Density 

2.156±0.06 g/cm3(Predicted)

storage temp. 

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

pka

11.54±0.40(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C7H4ClIN2/c8-5-1-2-10-7-4(5)3-6(9)11-7/h1-3H,(H,10,11)

InChIKey

PNYLOXIZBXVOPD-UHFFFAOYSA-N

SMILES

C12NC(I)=CC1=C(Cl)C=CN=2

Safety Information

Risk Statements 

41

Safety Statements 

26-39

HS Code 

2933399990

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-2-iodo- Usage And Synthesis

Synthesis

Step a) Synthesis of 4-chloro-2-iodo-1H-pyrrolo[2,3-b]pyridine: 4-chloro-2-iodo-1-methoxymethyl-1H-pyrrolo[2,3-b]pyridine (20 g, 62 mmol, 1 eq.) was dissolved in anhydrous dichloromethane (300 mL) under ice-bath cooling, and bromo catecholborane (16.06 g, 200 mL. 80 mmol, 1.3 equiv) to the solution. The reaction mixture initially showed a bright yellow color and rapidly changed to a thick suspension. After 1.5 hours of reaction, the solvent was removed by evaporation under reduced pressure. Potassium acetate (182 g, 1863 mmol, 30 eq.) and ethanol (400 mL) were added to the residue and the suspension was stirred at room temperature for 24 hours. Subsequently, ethanol was removed by evaporation under reduced pressure and the crude product was ground with water (400 mL) for 24 hours and washed with saturated sodium bicarbonate solution. The solid was collected by filtration and dried under vacuum to give 4-chloro-2-iodo-1H-pyrrolo[2,3-b]pyridine white solid (14.1 g, 82% yield). The product can be used directly in the subsequent reaction without further purification.

References

[1] Patent: WO2011/75613, 2011, A1. Location in patent: Page/Page column 58-59
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 20, p. 4730 - 4734

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-2-iodo-(940948-29-8)Related Product Information

• 4-Chloro-2-pyridinemethanamine
• 4-chloro-1H-indole-2-carboxylic acid
• 4-CHLORO-2-METHYLPYRIMIDINE
• 4-chloro-2-methylpyrido[2,3-d]pyrimidine
• 4-CHLORO-2-PHENYLPYRIDINE
• 1-BOC-PYRROLIDINE-3-CARBOXYLIC ACID
• 4-CHLORO-1,3-DIHYDRO-INDOL-2-ONE
• 4-Chloro-2-iodopyridine
• 4-Chloro-2-MethylpyriMidine-5-carbonitrile
• 5-chloro-3-methylsulfanyl-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene
• 4-Chloro-2,3-difluoropyridine
• 1H-Indole-2-carboxylic acid, 4-chloro-, Methyl ester
• Pyrimidine, 4-chloro-2-methoxy- (9CI)
• 4-Chloro-2,8-diMethylquinazoline
• 4-Chloro-2-fluoronicotinaldehyde
• 4-Chloro-2-methylfuro[3,2-d]pyrimidine
• 4-chloro-2-methylquinazoline
• 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-2-iodo-