[ CAS No. 1258833-77-0 ]

Name: 1258833-77-0|6-Bromo-8-fluoroisoquinoline|98%
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Product Details of [ 1258833-77-0 ]

CAS No. :	1258833-77-0	MDL No. :	MFCD28125257
Formula :	C₉H₅BrFN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	226.05 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 1258833-77-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1258833-77-0 ]

* 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 [ 1258833-77-0 ]

[ 1258833-77-0 ] Synthesis Path-Downstream 1~12

1
[ 57848-46-1 ]
[ 1258833-77-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: toluene / Dean-Stark; Reflux 2: triethylamine; dmap / dichloromethane / 24 h / 20 °C 3: Aluminum Chloride / dichloromethane / 29 h / -5 - 20 °C
	Multi-step reaction with 3 steps 1.1: toluene / Reflux 1.2: 12 h / 0 - 20 °C 2.1: triethylamine; dmap / dichloromethane / 24 h / 20 °C 3.1: Aluminum Chloride / dichloromethane / 29 h / -5 - 20 °C
	Multi-step reaction with 4 steps 1: toluene / 16 h / Reflux; Dean-Stark 2: sodium tetrahydridoborate / methanol / 4 h / 20 °C / Cooling with ice 3: dmap; triethylamine / dichloromethane / 4 h / 20 °C / Cooling with ice 4: Aluminum Chloride / dichloromethane / 20 °C / Schlenk technique; Cooling with ice

Multi-step reaction with 4 steps 1: toluene / 16 h / 140 °C 2: methanol; sodium tetrahydridoborate / 0 - 20 °C 3: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 4: Aluminum Chloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: CALITOR SCIENCES LLC; SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2014/89324, 2014, A1
[2]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD; CALITOR SCIENCES LLC - CN104016979, 2017, B
[3]Lenstra, Danny C.; Damen, Eddy; Leenders, Ruben G. G.; Blaauw, Richard H.; Rutjes, Floris P. J. T.; Wegert, Anita; Mecinović, Jasmin [ChemMedChem, 2018, vol. 13, # 14, p. 1405 - 1413]
[4]Current Patent Assignee: SHANGHAI ZHIMENG PHARMACEUTICAL TECH; SHANGHAI ZHIMENG BIOPHARMA - CN114057641, 2022, A

2
[ 1183945-15-4 ]
[ 1258833-77-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 24 h / 20 °C 2: Aluminum Chloride / dichloromethane / 29 h / -5 - 20 °C
	Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane / 4 h / 20 °C / Cooling with ice 2: Aluminum Chloride / dichloromethane / 20 °C / Schlenk technique; Cooling with ice
	Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 2: Aluminum Chloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: CALITOR SCIENCES LLC; SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2014/89324, 2014, A1 Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD; CALITOR SCIENCES LLC - CN104016979, 2017, B
[2]Lenstra, Danny C.; Damen, Eddy; Leenders, Ruben G. G.; Blaauw, Richard H.; Rutjes, Floris P. J. T.; Wegert, Anita; Mecinović, Jasmin [ChemMedChem, 2018, vol. 13, # 14, p. 1405 - 1413]
[3]Current Patent Assignee: SHANGHAI ZHIMENG PHARMACEUTICAL TECH; SHANGHAI ZHIMENG BIOPHARMA - CN114057641, 2022, A

3
[ 1613147-80-0 ]
[ 1258833-77-0 ]

Yield	Reaction Conditions	Operation in experiment
32%	With aluminum (III) chloride In dichloromethane at -5 - 20℃; for 29h;	14.3 Step 3) 6-bromo-8-fluoroisoquinoline To a suspension of aluminium chloride (2 g, 15 mmol) in DCM (15 mL) was added N-(4-bromo-2-fluorobenzyl)-N-(2,2-dimethoxyethyl)benzenesulfonamide (1.3 g, 3 mmol) in DCM (15 mL) at -5 °C. The reaction was stirred at rt for 29 h, then quenched with 10% HC1 at -10 °C, and extracted with DCM (20 mL x 3). The combined organic phases were washed with brine (20 mL), dried over anhydrous a2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 3/1) to give the title compound as a yellow solid (0.22 g, 32%). MS (ESI, pos. ion) m/z: 226 [M + H]+; NMR (400 MHz, i/6-DMSO) δ (ppm): 9.48 (s, 1H), 8.63-8.62 (d, J= 5.6 Hz, 1H), 7.81 (s, 1H), 7.58-7.57 (d, J= 5.6 Hz, 1H), 7.40-7.38 (dd, J= 1.6 Hz, 9.6 Hz, 1H).
32%	With aluminum (III) chloride In dichloromethane at -5 - 20℃; for 29h;	14.3 Step 3) Preparation of 6-bromo-8-fluoroisoquinoline Aluminum trichloride (2.0 g, 15 mmol)Was suspended in dichloromethane (15 mL)The solution was cooled to -5 ° C,To this was added N- (4-bromo-2-fluorobenzyl) -N- (2,2-dimethoxyethyl) benzenesulfonamide (1.3 g, 3 mmol)In dichloromethane (15 mL).The reaction solution was stirred at room temperature for 29 hours,Cooled to -10 ° C,Plus 10% hydrochloric acid quenching,And extracted with dichloromethane (20 mL x 3)take. The combined organic phases were washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column(Petroleum ether / ethyl acetate (v / v) = 3/1)The title compound was obtained as a yellow solid (0.22 g, 32%).

4
[ 1258833-77-0 ]
[ 1339780-81-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium tetrahydridoborate In glacial acetic acid at 20℃; for 3h;	14.4 Step 4) 6-bromo-8-fluoro-1,2,3,4-tetrahydroisoquinoline To a solution of 6-bromo-8-fluoroisoquinoline (0.22 g, 0.97 mmol) in HOAc (5 mL) was added NaBH4 (129 mg, 3.41 mmol) in portions. The reaction was stirred at rt for 3 h, then treated with saturated aqueous aHC03 until pH 8 and extracted with DCM (20 mL x 3). The combined organic phases were washed with brine (20 mL), dried over anhydrous Na2S04, filtered, concentrated in vacuo, and dried in vacuo to afford the title compound as a yellow solid (0.22 g, 98%). MS (ESI, pos. ion) m/z: 230 [M + H]+; NMR (400 MHz, i/6-DMSO) δ (ppm): 7.26-7.23 (dd, J= 1.6 Hz, 9.2 Hz, 1H), 7.17 (s, 1H), 3.75 (s, 2H), 2.89-2.86 (t, J= 6.0 Hz, 2H), 2.68-2.65 (t, J= 5.6 Hz, 2H).
98%	With sodium tetrahydridoborate; glacial acetic acid at 20℃; for 3h;	14.4 Step 4) Preparation of 6-bromo-8-fluoro-1,2,3,4-tetrahydroisoquinoline 6-bromo-8-fluoroisoquinoline (0.22 g, 0.97 mmol)Was dissolved in acetic acid (5 mL)To this was added sodium borohydride (129 mg, 3.41 mmol) in portions.The reaction solution was stirred at room temperature for 3 hours,After adjusting the pH to 8 with saturated sodium bicarbonate solution,Extraction with dichloromethane (20 mL x3).The combined organic phases were washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure and dried in vacuo.The title compound was obtained as a yellow solid (0.22 g, 98%).
	With sodium tetrahydridoborate; glacial acetic acid In tetrahydrofuran at 20℃; for 4h; Cooling with ice;

With sodium tetrahydridoborate; glacial acetic acid at 0 - 20℃; Inert atmosphere;

8.5 Step 5. Compound 7 Compound 6 (2.6 g, 11.5 mmol, 1.0 eq) was dissolved in acetic acid (40 mL), and the temperature was lowered to 0 °C under nitrogen protection, and sodium borohydride (1.3 g, 34.5 mmol, 3.0 eq) was added.The reaction solution was warmed to room temperature and stirred for 2 hours, diluted with water (200 mL), cooled to 0° C., adjusted to pH 10 with sodium carbonate, and extracted with ethyl acetate (3×200 mL).The combined organic phases were washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated to obtain crude compound 7 (3.0 g), which was used in the next reaction without purification.

Reference： [1]Current Patent Assignee: CALITOR SCIENCES LLC; SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2014/89324, 2014, A1 Location in patent: Paragraph 0251
[2]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD; CALITOR SCIENCES LLC - CN104016979, 2017, B Location in patent: Paragraph 0661; 0662; 0663; 0664
[3]Lenstra, Danny C.; Damen, Eddy; Leenders, Ruben G. G.; Blaauw, Richard H.; Rutjes, Floris P. J. T.; Wegert, Anita; Mecinović, Jasmin [ChemMedChem, 2018, vol. 13, # 14, p. 1405 - 1413]
[4]Current Patent Assignee: SHANGHAI ZHIMENG PHARMACEUTICAL TECH; SHANGHAI ZHIMENG BIOPHARMA - CN114057641, 2022, A Location in patent: Paragraph 0181-0182; 0194-0196

5
[ 1258833-77-0 ]
[ 1613147-81-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium tetrahydridoborate / glacial acetic acid / 3 h / 20 °C 2: anhydrous sodium carbonate / tetrahydrofuran; water monomer / 20 °C
	Multi-step reaction with 2 steps 1: sodium tetrahydridoborate; glacial acetic acid / 3 h / 20 °C 2: anhydrous sodium carbonate / tetrahydrofuran; water monomer / 20 °C
	Multi-step reaction with 2 steps 1: glacial acetic acid; sodium tetrahydridoborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C

Multi-step reaction with 2 steps 1: sodium tetrahydridoborate; glacial acetic acid / 0 - 20 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C

6
[ 1258833-77-0 ]
[ 1613147-82-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium tetrahydroborate / acetic acid / 3 h / 20 °C 2: sodium carbonate / tetrahydrofuran; water / 20 °C 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 80 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: sodium tetrahydroborate; acetic acid / 3 h / 20 °C 2: sodium carbonate / tetrahydrofuran; water / 20 °C 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 80 °C / Inert atmosphere

7
[ 1258833-77-0 ]
[ 1613147-83-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: sodium tetrahydroborate / acetic acid / 3 h / 20 °C 2: sodium carbonate / tetrahydrofuran; water / 20 °C 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane / 80 °C / Inert atmosphere 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,2-dimethoxyethane; water / 7 h / 95 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: sodium tetrahydroborate; acetic acid / 3 h / 20 °C 2: sodium carbonate / tetrahydrofuran; water / 20 °C 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane / 80 °C / Inert atmosphere 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / water; 1,2-dimethoxyethane / 7 h / 95 °C / Inert atmosphere

8
[ 1258833-77-0 ]
[ 1613147-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: sodium tetrahydroborate / acetic acid / 3 h / 20 °C 2: sodium carbonate / tetrahydrofuran; water / 20 °C 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane / 80 °C / Inert atmosphere 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,2-dimethoxyethane; water / 7 h / 95 °C / Inert atmosphere 5: hydrogenchloride / ethyl acetate / 4 h / 0 - 20 °C
	Multi-step reaction with 5 steps 1: sodium tetrahydroborate; acetic acid / 3 h / 20 °C 2: sodium carbonate / tetrahydrofuran; water / 20 °C 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane / 80 °C / Inert atmosphere 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / water; 1,2-dimethoxyethane / 7 h / 95 °C / Inert atmosphere 5: hydrogenchloride / ethyl acetate / 4 h / 0 - 20 °C

9
[ 2013582-59-5 ]
[ 1258833-77-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 20 - 80 °C 2: aluminum (III) chloride / dichloromethane / 16 h / -5 - 20 °C

Reference： [1]Current Patent Assignee: SHANGHAI YINGLI PHARM; SHANGHAI YINGLI PHARMACEUTICAL - EP3275867, 2018, A1

10
[ 2013582-60-8 ]
[ 1258833-77-0 ]

Yield	Reaction Conditions	Operation in experiment
31%	With aluminum (III) chloride In dichloromethane at -5 - 20℃; for 16h;	Synthesis of compound 9-d At -5°C, compound 9-e (1.50mg, 3.18mmol) was added to a mixture of AlCl3 (2.0g, 15mmol) in DCM (20mL).The mixture was reacted for 16hrs at room temperature, followed by adding 2M HCl aqueous solution (20mL), extractedwith DCM (30mL33). The organic phases were combined, washed in turn with water (10mL33) and saturated brine(20mL), dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure. The residue waspurified by silica column chromatography (PE:EA = 7:1) to give compound 9-d (220mg, yield 31%). LC-MS (ESI): m/z= 226 [M+H]+.

Reference： [1]Current Patent Assignee: SHANGHAI YINGLI PHARM; SHANGHAI YINGLI PHARMACEUTICAL - EP3275867, 2018, A1 Location in patent: Paragraph 0130; 0133

11
[ 1258833-77-0 ]
[ 2013582-61-9 ]

Yield	Reaction Conditions	Operation in experiment
64%	With N-iodo-succinimide; acetic acid; trifluoroacetic acid at 80℃; for 6h;	Synthesis of compound 9-c Compound 9-d (200mg, 0.89mmol) and N-iodosuccinimide (300mg, 1.33mmol) were dissolved in acetic acid (10mL) and trifluoroacetic acid (2mL), the mixture was reacted for 6hrs at 80 °C. The mixture was cooled to roomtemperature, concentrated under reduced pressure to remove the solvent. The residue was purified by silica columnchromatography (PE:EA = 8:1) to give compound 9-c (200mg, yield 64%). LC-MS (ESI): m/z = 352 [M+H]+.

Reference： [1]Current Patent Assignee: SHANGHAI YINGLI PHARM; SHANGHAI YINGLI PHARMACEUTICAL - EP3275867, 2018, A1 Location in patent: Paragraph 0130; 0134

12
[ 1258833-77-0 ]
[ 2013582-62-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-iodo-succinimide; acetic acid; trifluoroacetic acid / 6 h / 80 °C 2: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,2-dimethoxyethane / 4 h / 50 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SHANGHAI YINGLI PHARM; SHANGHAI YINGLI PHARMACEUTICAL - EP3275867, 2018, A1

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Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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. 1258833-77-0 ]

Quality Control of [ 1258833-77-0 ]

Related Doc. of [ 1258833-77-0 ]

Product Details of [ 1258833-77-0 ]

Safety of [ 1258833-77-0 ]

Application In Synthesis of [ 1258833-77-0 ]

[ 1258833-77-0 ] Synthesis Path-Downstream 1~12

Related Functional Groups of [ 1258833-77-0 ]

Fluorinated Building Blocks

Bromides

Related Parent Nucleus of [ 1258833-77-0 ]

Isoquinolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1258833-77-0 ]

Related Parent Nucleus of
[ 1258833-77-0 ]