Identification	Physical Data	Spectra
Route of Synthesis (ROS)	Safety and Hazards	Other Data

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Identification

Product Name	6-Chloro-1H-pyrazolo[4,3-c]pyridine
IUPAC Name	6-chloro-1H-pyrazolo[4,3-c]pyridine
Molecular Structure
CAS Registry Number	1206979-33-0
MDL Number	MFCD17010105
Synonyms	6-Chloro-1H-pyrazolo[4,3-c]pyridine 1206979-33-0 DTXSID40718894 6-Chloro-1H-pyrazolo(4,3-c)pyridine DTXCID90669640 808-339-3 MFCD17010105 SCHEMBL5066090 AAJIQIWPVIWCGA-UHFFFAOYSA-N BCP05299 BBL100380 STL554174 AKOS015919537 CS-W019595 PB25597 SY020932 TS-02049 DB-050724 EN300-97955
Molecular Formula	C6H4ClN3
Molecular Weight	153.57
InChI	InChI=1S/C6H4ClN3/c7-6-1-5-4(2-8-6)3-9-10-5/h1-3H,(H,9,10)
InChI Key	AAJIQIWPVIWCGA-UHFFFAOYSA-N
SMILES	CC1=C2C(=CN=C1Cl)C=NN2

Patent Information
Patent ID	Title	Publication Date
US2014/171405	Fused Pyrazoles as FGFR Inhibitors	2014
WO2013/17479	PYRAZOLO[4,3-C]PYRIDINE DERIVATIVES AS JAK INHIBITORS	2013
WO2013/17480	PYRAZOLO[4,3-C]PYRIDINE DERIVATIVES AS JAK INHIBITORS	2013

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Physical Data

Appearance	Light yellow to brown solid
Solubility	Soluble in ethanol

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Spectra

Description (NMR Spectroscopy)	Nucleus (NMR Spectroscopy)	Solvents (NMR Spectroscopy)	Frequency (NMR Spectroscopy), MHz
Chemical shifts	1H	dimethylsulfoxide-d6	400

6-Chloro-1H-pyrazolo[4,3-c]pyridine CAS#: 1206979-33-0 NMR

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Route of Synthesis (ROS)

Conditions	Yield
With 4-methylbenzene-1-sulfonyl chloride In 1,4-dioxane at 110℃; Experimental Procedure 76.A 6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine A mixture of 6-chloro-1H-pyrazolo[4,3-c]pyridine (11.5 g, 0.075 mol) and 3,4-dihydro-2H-pyran (19 g, 0.225 mol) and Tos-OH (0.13 g 0. 75 mmol) in 1,4-dioxane (175 mL) was heated at 110 °C overnight. The mixture was cooled to room temperature and concentrated. The crude product was purified by column chromatography on silica gel (petroleum ether ethylacetate 20:0~20: 1) to afford a mixture of 6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine and 6-chloro-2-(tetrahydro-2H-pyran-2-yl)-2H-pyrazolo[4,3-c]pyridine (13.5 g, yield 76 %) MS (ESI) m/z: m/z: 238 [M+1]+.	76%
With toluene-4-sulfonic acid In 1,4-dioxane at 110℃; for 18h;	76%
With toluene-4-sulfonic acid In dichloromethane for 24h; Reflux; Experimental Procedure 149 Preparation 1496-Chloro-1 -(tetrahydro-2H-pyran-2-yl)- 1 H-pyrazolo[4,3-c]pyridine Preparation 1496-Chloro-1 -(tetrahydro-2H-pyran-2-yl)- 1 H-pyrazolo[4,3-c]pyridine10684] To a solution of 6-chloro-1H-pyrazolo[4,3-c]pyri- dine (75 g, 488.37 mmol) in DCM (2 L) was added dihydropyran (66.98 mE, 732.56 mmol) followed by para-toluenesulfonic acid (18.58 g, 97.67 mmol) and the reaction was heated to reflux for 18 hours. Further para-toluenesulfonic acid (0.1 eq) and dihydropyran (0.75 eq) were added and the reaction continued heating at reflux for 6 hours. The reaction was cooled and quenched with saturated aqueous sodium bicarbonate solution. The organic layer was collected, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 17% EtOAc in hexanes followed by trituration with ether to afford the title compound as a pale yellow solid (83 g, 72%). ‘H NMR (400 MHz, DMSO-d5): öppm 1.59 (m, 2H), 1.71 (m, 1H), 2.02 (m, 2H), 2.29 (m, 1H), 3.74 (m, 1H), 3.89 (m, 1H), 5.91 (m, 1H), 7.93 (s, 1H), 8.38 (s, 1H), 8.94 (s, 1H).	72%
With toluene-4-sulfonic acid In dichloromethane at 45℃; for 16h; Experimental Procedure 1 Step 1: 6-(hloro-l -(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo|4,-c|pyridine [00297] A mixture of 6-chloro-1H-pyrazolo[4,3-c]pyridine(3 g, 19.54 mmol),DHP (5.4 mL, 58.61 mmol), and TsOH H2O (743 mg, 3.91 mmol) in DCM (40 mL) was stirred at 45 °C for 16 h, allowed to cool to rt, adjusted to pH=7 with sat. aq. NaHCO3, and then extracted with DCM (3 x30 mL). The combined organic layers were washed with brine (30 mL), dried (Na2SO4), filtered, concentrated, and then purified by silica gel chromatography (petroleum ether/ethyl acetate=30: 1 to 3 : 1) to give 6-chloro- 1 -(tetrahydro-2H -pyran-2-yl)- l H-pyrazolo[4,3-c]pyridine (2.8 g, 60%) as a yellow solid. 1HNMR(400 MHz, DDDMSO-d δ6): 8.95 (d, 1H), 8.38 (s, 1H), 7.93 (s, 1H), 5.91 (dd, 1H), 3.90-3.87 (m, 1H), 3.79-3.73 (m, 1H), 2.36-2.32 (m, 1H), 2.03-1.95 (m, 2H), 1.73-1.69 (m, 1H), 1.60-1.55 (m, 2H); LCMS: 238.1 [M+H]+.	60%
With methanesulfonic acid In tetrahydrofuran; dichloromethane at 20 – 50℃; Experimental Procedure 24.1 6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine At r.t. to a suspension of 6-chloro-1H-pyrazolo[4,3-c]pyridine (0.5 g, 3 mmol) (Frontier Cat. No. Z13659) in methylene chloride (3 mL) and THF (1 mL) was added methanesulfonic acid (42 μL, 0.65 mmol), followed by dihydropyran (0.89 mL, 9.8 mmol). The mixture was stirred at r.t. for 2 h., and then at 50° C. overnight. After cooling the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.8 g). LCMS (M+H)+=238.0; LCMS (M-84+H)+=154.0/156.0.	0.8 g

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Safety and Hazards

Pictogram(s)
Signal	Warning
GHS Hazard Statements	H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement Codes	P264, P270, P301+P317, P330, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.)

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Other Data

Transportation	Under room temperature away from light
Storage	Under room temperature away from light
Shelf Life	2 years

Druglikeness
Lipinski rules component
Molecular Weight	153.571
logP	1.607
HBA	3
HBD	1
Matching Lipinski Rules	4
Veber rules component
Polar Surface Area (PSA)	41.57
Rotatable Bond (RotB)	0
Matching Veber Rules	2

Use Pattern

The compound, featuring a pyrazolopyridine structure, is primarily used as a pharmaceutical intermediate. It plays a crucial role in the synthesis of targeted kinase inhibitors, such as PI3K, JAK, and BTK inhibitors, as well as drugs for central nervous system disorders. It often serves as a core scaffold in the development of anti-cancer, anti-inflammatory, antiviral, and neurological therapeutics. In drug discovery, this structure is highly valued for its biological activity and versatility. The presence of a chlorine atom allows for further functionalization through reactions such as Suzuki or Buchwald couplings, enabling the construction of more complex molecules. Additionally, this compound is frequently employed in early-stage drug research, particularly in high-throughput screening (HTS) and structure-activity relationship (SAR) studies, making it a valuable tool in the identification and optimization of lead compounds.

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