[ CAS No. 1374652-62-6 ] {[proInfo.proName]}

Name: 1374652-62-6|5-Bromo-7-methoxy-1H-indazole|96%
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3d Animation Molecule Structure of 1374652-62-6

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Quality Control of [ 1374652-62-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1374652-62-6 ]

SDS Specification

Alternatived Products of [ 1374652-62-6 ]

Product Details of [ 1374652-62-6 ]

CAS No. :	1374652-62-6	MDL No. :	MFCD11878570
Formula :	C₈H₇BrN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GLOTVIAEDAXCAT-UHFFFAOYSA-N
M.W :	227.06	Pubchem ID :	83669485
Synonyms :

Calculated chemistry of [ 1374652-62-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.29
TPSA :	37.91 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.73
Log Po/w (XLOGP3) :	2.22
Log Po/w (WLOGP) :	2.33
Log Po/w (MLOGP) :	1.58
Log Po/w (SILICOS-IT) :	2.66
Consensus Log Po/w :	2.1

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.14
Solubility :	0.166 mg/ml ; 0.000732 mol/l
Class :	Soluble
Log S (Ali) :	-2.65
Solubility :	0.507 mg/ml ; 0.00223 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.9
Solubility :	0.0287 mg/ml ; 0.000126 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.09

Safety of [ 1374652-62-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H320-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1374652-62-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1374652-62-6 ]

[ 1374652-62-6 ] Synthesis Path-Downstream 1~7

1
[ 1374652-62-6 ]
[ 2247450-87-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 12 h / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - CN108467386, 2018, A

2
[ 1374652-62-6 ]
[ 73183-34-3 ]
[ 2247451-15-4 ]

Yield	Reaction Conditions	Operation in experiment
63%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; for 12h; Inert atmosphere;	5.1 first step 7-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 5b 5-Bromo-7-methoxy-1H-carbazole 5a (1.63 g, 7.18 mmol) was added in sequence under an argon atmosphere."Prepared by the method disclosed in WO2013051632"), compound 1b (2.73g, 10.75mmol), potassium acetate (2.11g, 21.5mmol) and [1,1'-bis(diphenylphosphino)ferrocene] Palladium chloride (525 mg, 0.72 mmol) was dissolved in 40 mL of 1,4-dioxane solution.Heat to 110 ° C and stir for 12 hours. The reaction was stopped, cooled to room temperature, filtered, and the filtrate was concentrated.The residue was purified by silica gel chromatography using eluent system B.The title compound 5b (1.25 g, yield: 63.0%) was obtained.

Reference： [1]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - CN108467386, 2018, A Location in patent: Paragraph 0256; 0258; 0259; 0260; 0261

3
[ 348169-39-1 ]
5-bromo-7-methoxy-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28.5%	With acetic acid; sodium nitrite In water at 0 - 20℃;	Intermediate 4: 5-Bromo-7-methoxy-1H-indazole To a solution of 4-bromo-2-methoxy-6-methylaniline (5 g, 23.1 mmol, 1.0 eq) in glacial acetic acid (50 mL) at 0 °C was slowly added aqueous sodium nitrite solution (3.19 g, 46.3 mmol, 2.0 eq). The resulting reaction mixture was stirred at room temperature for overnight. The reaction was quenched with water (100 mL). The resulting mixture was extracted with ethyl acetate (3 x 100 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (0-50 % ethyl acetate / petroleum ether) to afford the 5-bromo-7- methoxy-1H-indazole as a red solid (1.5 g, 28.5 % yield)
	With acetic acid; sodium nitrite In water at 15℃; for 14h;	4 To a solution of 4-bromo-2-methoxy-6-methylaniline (8.00 g, 37.0 mmol) in AcOH (80 mL) and water (16 mL) was added sodium nitrite (3.83 g, 55.5 mmol) and the reaction stirred at 15 °C for 14 h. The mixture was concentrated in vacuo, the residue was neutralised using saturated aq. NaHCO3 (100 mL x 3) and extracted with EtOAc (250 mL x 3). The combined organic layers were washed with brine (80 mL x 2), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel using a Combiflash system, eluting with PE/EtOAc (75/25) to afford 5-bromo-7-methoxy- 1H-indazole (1.70 g, 17% yield) as a brown solid. 1HNMR (400MHz, DMSO-d6) d: 3.97 (s, 3H), 6.94 (s, 1H), 7.54 (s, 1H), 8.00 (s, 1H), 13.50 (s, 1H).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2021/240423, 2021, A1 Location in patent: Page/Page column 51; 52
[2]Current Patent Assignee: BIOGEN IDEC INC. - WO2020/263967, 2020, A1 Location in patent: Page/Page column 83

4
[ 1374652-62-6 ]
[ 2642618-56-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 80 °C / Microwave irradiation 2: 1-dodecylthiol; lithium tert-butoxide / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / 100 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: Syngenta (in: Sinochem Holdings); SINOCHEM HOLDINGS CORPORATION LTD - WO2021/94416, 2021, A1

5
[ 1374652-62-6 ]
[ 2642617-71-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 80 °C / Microwave irradiation 2: 1-dodecylthiol; lithium tert-butoxide / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 1 h / 80 °C

Reference： [1]Current Patent Assignee: Syngenta (in: Sinochem Holdings); SINOCHEM HOLDINGS CORPORATION LTD - WO2021/94416, 2021, A1

6
[ 1374652-62-6 ]
[ 2642617-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 80 °C / Microwave irradiation 2: 1-dodecylthiol; lithium tert-butoxide / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 1 h / 80 °C 4: N-chloro-succinimide / acetonitrile / 2 h / 80 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: Syngenta (in: Sinochem Holdings); SINOCHEM HOLDINGS CORPORATION LTD - WO2021/94416, 2021, A1

7
[ 406-81-5 ]
5-bromo-7-methoxy-1H-indazole [ No CAS ]
5-bromo-7-methoxy-1-(4,4,4-trifluorobutyl)indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 1h;Microwave irradiation;	To a solution of 5-bromo-7-methoxy-1H-indazole (1.00 g, 4.40 mmol) in N,N- dimethylformamide (16 mL) was added 4-bromo-1, 1,1 -trifluoro-butane (0.865 mL, 7.05 mmol) followed by Cs2CO3 (2.55 g, 13.2 mmol). The reaction was heated under microwave irradiation at 80C for 1 hour. The reaction mixture was poured into water and diluted with EtOAc. The phases were separated and the aqueous was extracted into EtOAc (x2). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by column chromatography on silica gel using a gradient of 0- 70% EtOAc/cyclohexane to give the desired product (1.10 g, 74%) as a yellow solid. (0146) 1H NMR (400 MHz, CDCI3) δ 7.85 (s, 1H), 7.43 (d, 1H), 6.80 (d, 1H), 4.68 (t, 2H), 3.97 (s, 3H), 2.19 - 2.02 (m, 4H).

Reference： [1]Patent: WO2021/94416,2021,A1 .Location in patent: Page/Page column 33

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Isomers

Technical Information

• Acetal Formation • Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Convert Haloalkanes into Alcohols by SN2 • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Ethers Synthesis from Alcohols with Strong Acids • Friedel-Crafts Alkylation of Benzene with Haloalkanes • General Reactivity • Grignard Reaction • Grignard Reagents Transform Esters into Alcohols • Halogenation of Alkenes • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Methylation of Ammonia • Nomenclature of Ethers • Preparation of Ethers • Primary Ether Cleavage with Strong Nucleophilic Acids • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reactions of Ethers • Ring Opening of Oxacyclopropane • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Synthesis of Alcohols from Tertiary Ethers • The Nucleophilic Opening of Oxacyclopropanes • Williamson Ether Syntheses

Historical Records

Related Functional Groups of
[ 1374652-62-6 ]

Bromides

[ 938062-01-2 ]

4-Bromo-7-methoxy-1H-indazole

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[ 1351668-22-8 ]

4-Bromo-7-ethoxy-1H-indazole

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[ 1374651-60-1 ]

6-Bromo-7-methoxy-1H-indazole

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[ 885520-83-2 ]

4-Bromo-6-methoxy-1H-indazole

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[ 885519-21-1 ]

6-Bromo-4-methoxy-1H-indazole

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Ethers

[ 938062-01-2 ]

4-Bromo-7-methoxy-1H-indazole

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[ 1351668-22-8 ]

4-Bromo-7-ethoxy-1H-indazole

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[ 1374651-60-1 ]

6-Bromo-7-methoxy-1H-indazole

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[ 885520-83-2 ]

4-Bromo-6-methoxy-1H-indazole

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[ 885519-21-1 ]

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Related Parent Nucleus of
[ 1374652-62-6 ]

Indazoles

[ 938062-01-2 ]

4-Bromo-7-methoxy-1H-indazole

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[ 1351668-22-8 ]

4-Bromo-7-ethoxy-1H-indazole

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[ 1374651-60-1 ]

6-Bromo-7-methoxy-1H-indazole

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[ 885520-83-2 ]

4-Bromo-6-methoxy-1H-indazole

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[ 885519-21-1 ]

6-Bromo-4-methoxy-1H-indazole

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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
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P233	Keep container tightly closed.
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P321
P322
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P342	If experiencing respiratory symptoms:
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1374652-62-6 ] {[proInfo.proName]}

Quality Control of [ 1374652-62-6 ]

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Product Details of [ 1374652-62-6 ]

Calculated chemistry of [ 1374652-62-6 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1374652-62-6 ]

Application In Synthesis of [ 1374652-62-6 ]

[ 1374652-62-6 ] Synthesis Path-Downstream 1~7

Technical Information

Related Functional Groups of [ 1374652-62-6 ]

Bromides

Ethers

Related Parent Nucleus of [ 1374652-62-6 ]

Indazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1374652-62-6 ]

Related Parent Nucleus of
[ 1374652-62-6 ]