4-Iodo-2-methoxypyridine-3-carboxaldehyde Chemical Properties

Boiling point:

328.3±42.0 °C(Predicted)

Density 

1.873±0.06 g/cm3(Predicted)

storage temp. 

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

pka

0.21±0.18(Predicted)

form 

Solid

Appearance

Light yellow to yellow Solid

Sensitive 

Light Sensitive

InChI

InChI=1S/C7H6INO2/c1-11-7-5(4-10)6(8)2-3-9-7/h2-4H,1H3

InChIKey

GNBKAOHTTIVAMT-UHFFFAOYSA-N

SMILES

C1(OC)=NC=CC(I)=C1C=O

CAS DataBase Reference

158669-26-2(CAS DataBase Reference)

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

4-Iodo-2-methoxypyridine-3-carboxaldehyde Usage And Synthesis

Uses

This compound is used in the synthesis of insulin-like growth factor 1-receptor inhibitors that display anti-tumor activity.

Uses

4-Iodo-2-methoxypyridine-3-carboxaldehyde is used in the synthesis of insulin-like growth factor 1-receptor inhibitors that display anti-tumor activity.

Synthesis

General procedure for the synthesis of 4-iodo-2-methoxypyridine-3-carboxaldehyde (DeTMS-PM): tert-butyl lithium (1.5 M in n-pentane, 6.9 mL, 9.16 x 1.1 mmol) was added slowly and dropwise to a solution of 2-methoxypyridine (1.00 g, 9.16 mmol) in dry THF (7.5 mL) at -75 °C to -60 °C and stirred at the same temperature for 1 hour. Subsequently, a solution of anhydrous THF (10 mL) of FEO (1.44 g, 9.16 x 1.2 mmol) was added dropwise at the same temperature and stirring was continued for 30 min. The temperature of the reaction system was raised to about -23 °C, ethylene glycol dimethyl ether (DME, organic synthesis grade, 7.5 mL) was added, followed by dropwise addition of n-butyllithium (1.6 M in hexane, 9.9 mL, 9.16 x 1.7 mmol), and the reaction was maintained between -15 °C and -25 °C and stirred for 2 hours at about -23 °C. The mixture was cooled to about -70 °C, a solution of iodine (4.42 g, 9.16 x 1.9 mmol) in DME (10 mL) was added quickly and stirred at about -70 °C for 30 minutes. After warming to room temperature, 10% Na2SO3 solution (in appropriate amount until the color of iodine disappeared) was added and stirred for 10 min, followed by extraction with water, brine and ethyl acetate (50 mL). The organic layer was separated, dried with Na2SO4, filtered and concentrated to dryness. The residue (brown solid) was dissolved in chloroform and purified by medium-pressure silica gel column chromatography (n-hexane: ethyl acetate = 1000:1 → 100:1). The desired grades were collected and concentrated to dryness to give DeTMS-PM (1.31 g, 4.98 mmol, 54%) as a yellow solid. The product was confirmed by 1H-NMR (400 MHz, CDCl3): δ 4.05 (3H, s, MeO), 7.54 (1H, d, J = 5.4 Hz, Aromatic-H), 7.85 (1H, d, J = 5.4 Hz, Aromatic-H), 10.21 (1H, s, CHO).IR (KBr) showed characteristic absorption peaks (cm-1): 2943, 1697 (CHO), 1543, 1458, 1362, 1015.EI-MS (m/z): 263 [M]+ (100%).

References

[1] Patent: EP1900740, 2008, A1. Location in patent: Page/Page column 14-15

4-Iodo-2-methoxypyridine-3-carboxaldehyde(158669-26-2)Related Product Information

• 4-Iodopyridine
• 4-Pyridinecarboxaldehyde
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• 4-Methoxybenzyl cyanide
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• pyridylaldehyde
• 4-IODO-2-METHOXYPYRIDINE
• 4-Iodo-3-methylpyridine
• 4-Iodo-2-methoxypyridine-3-carboxaldehyde