1H-Imidazo[4,5-c]pyridine, 4-chloro-7-fluoro- (9CI)

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1H-Imidazo[4,5-c]pyridine, 4-chloro-7-fluoro- (9CI) Basic information
Product Name:1H-Imidazo[4,5-c]pyridine, 4-chloro-7-fluoro- (9CI)
Synonyms:1H-Imidazo[4,5-c]pyridine, 4-chloro-7-fluoro- (9CI);3H-IMidazo[4,5-c]pyridine,4-chloro-7-fluoro-;4-chloro-7-fluoro-1H-iMidazo[4;4-CHLORO-7-FLUORO-1H-IMIDAZO[4,5-C]PYRIDINE;4-chloro-7-fluoro-3H-imidazo[4,5-c]pyridine
CAS:405230-97-9
MF:C6H3ClFN3
MW:171.56
EINECS:
Product Categories:
Mol File:405230-97-9.mol
1H-Imidazo[4,5-c]pyridine,  4-chloro-7-fluoro-  (9CI) Structure
1H-Imidazo[4,5-c]pyridine, 4-chloro-7-fluoro- (9CI) Chemical Properties
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
AppearanceWhite to off-white Solid
Safety Information
HS Code 2933998090
MSDS Information
1H-Imidazo[4,5-c]pyridine, 4-chloro-7-fluoro- (9CI) Usage And Synthesis
Synthesis
Triethyl orthoformate

122-51-0

2-Chloro-5-fluoro-3,4-pyridinediamine

405230-93-5

1H-Imidazo[4,5-c]pyridine,  4-chloro-7-fluoro-  (9CI)

405230-97-9

General procedure for the synthesis of 4-chloro-7-fluoro-1H-imidazo[4,5-c]pyridines from triethyl orthoformate and 2-chloro-3,4-diamino-5-fluoropyridine: sulfamic acid (187 mL, 4.15 mmol) was added to a solution of 2-chloro-5-fluoropyridine-3,4-diamine (670 mg, 4.15 mmol, commercially available from Bellen, Inc. Beijing, China) and triethyl orthoformate (2.76 mL, 16.6 mmol) in a solution of methanol (10 mL). The mixture was heated to reflux for 16 hours. After completion of the reaction, the mixture was cooled to room temperature, diluted with saturated aqueous NaHCO3 solution and extracted with dichloromethane (DCM). The DCM extracts were combined, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel column chromatography using a gradient elution of 0-20% methanol/DCM to afford the target product 4-chloro-7-fluoro-1H-imidazo[4,5-c]pyridine (560 mg, 3.26 mmol, 79% yield).

References[1] Patent: WO2018/97944, 2018, A1. Location in patent: Paragraph 0248; 0261; 0262
1H-Imidazo[4,5-c]pyridine, 4-chloro-7-fluoro- (9CI) Preparation Products And Raw materials
Raw materialsTriethyl orthoformate-->2-Chloro-5-fluoro-3,4-pyridinediamine-->Sulfamic acid-->Methanol
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