Structure of 956700-15-5
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only! Not for Human Use. We Do Not Sell to Patients.
Change View
| Size | Price | VIP Price |
DE Stock US Stock |
Asia Stock Global Stock |
In Stock |
| {[ item.pr_size ]}{[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | {[ item.p_spot_brand_remark ]} 1-2 weeks {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.p_spot_brand_remark ]} 1-2 weeks {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock Inquiry - | Login - + |
Please Login or Create an Account to: See VIP prices and availability
Asia Stock: Ship in 3-5 business days
EU Stock: ship in 0-1 business day
Global Stock: ship in 7-10 days
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
{[ item.p_spot_brand_remark ]}
1-2weeks
Inquiry
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ item.p_spot_brand_remark ]}
1-2weeks
Inquiry
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
Asia Stock: Ship in 3-5 business days
EU Stock: ship in 0-1 business day
Global Stock: ship in 7-10 days
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
| CAS No. : | 956700-15-5 |
| Formula : | C9H5BrFNO |
| M.W : | 242.05 |
| SMILES Code : | O=C1NC=C(F)C2=C1C=C(Br)C=C2 |
| English Name : | 7-Bromo-4-fluoroisoquinolin-1(2H)-one |
| MDL No. : | MFCD20526591 |
* 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.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 43% | With Selectfluor In acetonitrile at 80℃; for 6h; | 193; 237 Preparation of 7-bromo-4-fluoro-2H-isoquinolin-1-one (237a): To a solution of 7-bromo-2H-isoquinolin-l-one (3 g, 13.4 mmol) in ACN (30 mL) was added selectfluor (4.8 g,13.4 mmol) at rt. The reaction mixture was heated to 80 °C and stirred for 6 h. The resulting mixture was cooled to rt and purified by reversed-phase flash chromatography directly to afford the title compound as a yellow solid (1.4 g, 43%). LCMS ESI-MS m/z = 241 [M+H]+. |
| Multi-step reaction with 2 steps 1: Selectfluor / acetonitrile; water / 96 h / 20 °C 2: methanesulfonic acid / dichloromethane / 16 h / 20 °C | ||
| Multi-step reaction with 2 steps 1: Selectfluor / water; acetonitrile / 30 °C 2: methanesulfonic acid / dichloromethane / 20 °C |
| Multi-step reaction with 2 steps 1: Selectfluor; water / acetonitrile / 30 °C 2: methanesulfonic acid / dichloromethane |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 89.5% | With methanesulfonic acid In dichloromethane at 20℃; for 16h; | 2 Step 2: Synthesis of Compound WXBB-5 Compound WXBB-5-2 (3.00 g, 11.54 mmol, 1.00 eq) and methanesulfonic acid (7.76 g, 80.75 mmol, 5.75 mL, 7.00 eq) were dissolved in dichloromethane (50.00 mL). The mixture was reacted at 20° C. for 16 hours. After the reaction was completed, the reaction solution was added with dichloromethane (15 mL), washed successively with water (20 mL) and saturated brine (20 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was dried on a rotary evaporator under reduced pressure. The obtained crude product was slurried with ethyl acetate (10 mL) at 15° C. for 0.5 hour, filtered and the filter cake was dried. Compound WXBB-5 (2.50 g, 10.33 mmol, 89.50% yield) was obtained as a red solid, 1H NMR (400 MHz, DMSO-d6) ppm 7.46 (d, J=5.77 Hz, 1H) 7.71 (d, J=8.53 Hz, 1H) 8.01 (dd, J=8.53, 1.76 Hz, 1H) 8.30 (s, 1H) 11.37 (br. s., 1H). |
| 86% | With methanesulfonic acid In dichloromethane | 21.2 Step 2: To a stirred solution of 7-bromo-4-fluoro-3-hydroxyisoquinolin-l(2//)-one (1.50 g, 5.77 mmol) in DCM (15 mL) was added methanesulfonic acid (2.77 g, 28.84 mmol, 1.87 mL). The reaction mixture was stirred at room temperature overnight, diluted with DCM (20 mL) and washed with water (20 mL) and brine (20 mL). The organic phase was dried over anhydrousNa2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was purified by flash column chromatography on silica gel (eluting with ethyl acetate/petroleum ether from 0 to 80%) to give 7-bromo-4- I uoroi soqui nol i n- 1 (2/7)-onc (1.20 g, 86% yield) as a light yellow solid. LC-MS (ESI) [(M+H)+]: 242.1. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 52.23% | With 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) In lithium hydroxide monohydrate; acetonitrile at 30℃; | 21.3 Step 3: To a stirred solution of 7-bromo-4- I uoroi soqui nol i n- 1 (2/7)-onc (500.0 mg, 2.07 mmol) in MeCN/Water (22 mL, 10/1) was added selectfluor (804.4 mg, 2.27 mmol). The reaction mixture was stirred at 30 °C overnight, diluted with 20 mL of water, and extracted with DCM (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was purified by flash column chromatography on silica gel (eluting with EtOAc:petroleum ether from 0 to 90%) to give 7- bromo-4, 4-difluoro-3 -hydroxy-3, 4-dihydroisoquinolin-l(27/)-one 300.0 mg, 1.08 mmol, 52.23% yield) as a light yellow solid. LC-MS (ESI) [(M+H)+]: 278.1. |
| 52.23% | With 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) In lithium hydroxide monohydrate; acetonitrile at 30℃; | 21.3 Step 3: To a stirred solution of 7-bromo-4- I uoroi soqui nol i n- 1 (2/7)-onc (500.0 mg, 2.07 mmol) in MeCN/Water (22 mL, 10/1) was added selectfluor (804.4 mg, 2.27 mmol). The reaction mixture was stirred at 30 °C overnight, diluted with 20 mL of water, and extracted with DCM (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was purified by flash column chromatography on silica gel (eluting with EtOAc:petroleum ether from 0 to 90%) to give 7- bromo-4, 4-difluoro-3 -hydroxy-3, 4-dihydroisoquinolin-l(27/)-one 300.0 mg, 1.08 mmol, 52.23% yield) as a light yellow solid. LC-MS (ESI) [(M+H)+]: 278.1. |
| 52.23% | With lithium hydroxide monohydrate; 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) In acetonitrile at 30℃; | 21.3 Step 3: To a stirred solution of 7-bromo-4- I uoroi soqui nol i n- 1 (2/7)-onc (500.0 mg, 2.07 mmol) in MeCN/Water (22 mL, 10/1) was added selectfluor (804.4 mg, 2.27 mmol). The reaction mixture was stirred at 30 °C overnight, diluted with 20 mL of water, and extracted with DCM (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was purified by flash column chromatography on silica gel (eluting with EtOAc:petroleum ether from 0 to 90%) to give 7- bromo-4, 4-difluoro-3 -hydroxy-3, 4-dihydroisoquinolin-l(27/)-one 300.0 mg, 1.08 mmol, 52.23% yield) as a light yellow solid. LC-MS (ESI) [(M+H)+]: 278.1. |
| With 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) In lithium hydroxide monohydrate; acetonitrile at 20℃; for 16h; | 003.1 Step 1: Synthesis of Compound WX003-1 Compound WXBB-5 (2.50 g, 10.33 mmol, 1.00 eq) and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (4.39 g, 12.40 mmol, 1.20 eq) were dissolved in acetonitrile (150.00 mL) and water (10.00 mL). The mixture was reacted at 20° C. for 16 hours. After the reaction was completed, the reaction solution was added with water (300 mL), and extracted with dichloromethane (DCM) (300 mL). The organic phases were combined, washed with saturated brine (30 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was dried on a rotary evaporator under reduced pressure. Compound WX003-1 was obtained, 1H NMR (400 MHz, DMSO-d6) δ ppm 5.06 (d, J=2.51 Hz, 1H) 5.33 (s, 1H) 7.72 (dd, J=8.28, 1.76 Hz, 1H) 7.85 (d, J=8.03 Hz, 1H) 7.99 (d, J=8.53 Hz, 1H) 8.06 (s, 1H) 8.15 (d, J=2.01 Hz, 1H) 9.25 (br. s., 1H). |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) / acetonitrile; lithium hydroxide monohydrate / 16 h / 20 °C 2: methanesulfonic acid; triethylsilane / dichloromethane / 32 h / 15 °C | ||
| Multi-step reaction with 2 steps 1: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) / lithium hydroxide monohydrate; acetonitrile / 30 °C 2: methanesulfonic acid; triethylsilane / dichloromethane | ||
| Multi-step reaction with 2 steps 1: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate); lithium hydroxide monohydrate / acetonitrile / 30 °C 2: methanesulfonic acid; triethylsilane / dichloromethane |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: Selectfluor / acetonitrile; water / 16 h / 20 °C 2: methanesulfonic acid; triethylsilane / dichloromethane / 32 h / 15 °C 3: 8-quinolinol; copper(l) iodide; potassium carbonate / dimethyl sulfoxide / 16 h / 130 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 4 steps 1: Selectfluor / acetonitrile; water / 16 h / 20 °C 2: methanesulfonic acid; triethylsilane / dichloromethane / 32 h / 15 °C 3: 8-quinolinol; copper(l) iodide; potassium carbonate / dimethyl sulfoxide / 16 h / 130 °C / Inert atmosphere 4: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With Selectfluor In N,N-dimethyl acetamide at 150℃; Microwave irradiation; | 1 6-Bromo-4-fluoroisoquinolin-1(2H)-one General procedure: A mixture of 6-bromoisoquinolin~1 (2H)-one (385 g, 1.63 mmol), 1-chloromethyl~4~ fluoro-1 ,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) [Selectfluor] (578 mg, 1.63 mmol), and dimethylacetamide (3.5 mL) was heated in a microwave for 15 minutes at 150°C. This was repeated three more times. The four runs were combined and partitioned between EtOAc (100 mL) and water (100 mL). The aqueous layer was extracted with EtOAc (2 x 100 mL), and the combined organic extracts were washed with brine, dried (Na2SG4) and concentrated, and the residue was purified by silica chromatography (0-50% EtOAc in Hex) to give the title compound (230 mg, 25%).1H NMR (500 MHz, DMSO-cfe) d ppm 1 1.30 (br s,1 H) 8.12 (dd, 1 H) 7.91 (d, 1 H) 7.78 (dd, 1 H) 7.47 (m, 1 H); MS (m/z): 241.9 [M+1]. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 86% | With methanesulfonic acid In dichloromethane at 20℃; | 21.2 Step 2: To a stirred solution of 7-bromo-4-fluoro-3-hydroxyisoquinolin-l(2//)-one (1.50 g, 5.77 mmol) in DCM (15 mL) was added methanesulfonic acid (2.77 g, 28.84 mmol, 1.87 mL). The reaction mixture was stirred at room temperature overnight, diluted with DCM (20 mL) and washed with water (20 mL) and brine (20 mL). The organic phase was dried over anhydrousNa2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was purified by flash column chromatography on silica gel (eluting with ethyl acetate/petroleum ether from 0 to 80%) to give 7-bromo-4- I uoroi soqui nol i n- 1 (2/7)-onc (1.20 g, 86% yield) as a light yellow solid. LC-MS (ESI) [(M+H)+]: 242.1. |
| 86% | With methanesulfonic acid In dichloromethane at 20℃; | 21.2 Step 2: To a stirred solution of 7-bromo-4-fluoro-3-hydroxyisoquinolin-l(2//)-one (1.50 g, 5.77 mmol) in DCM (15 mL) was added methanesulfonic acid (2.77 g, 28.84 mmol, 1.87 mL). The reaction mixture was stirred at room temperature overnight, diluted with DCM (20 mL) and washed with water (20 mL) and brine (20 mL). The organic phase was dried over anhydrousNa2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was purified by flash column chromatography on silica gel (eluting with ethyl acetate/petroleum ether from 0 to 80%) to give 7-bromo-4- I uoroi soqui nol i n- 1 (2/7)-onc (1.20 g, 86% yield) as a light yellow solid. LC-MS (ESI) [(M+H)+]: 242.1. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) / lithium hydroxide monohydrate; acetonitrile / 30 °C 2: methanesulfonic acid; triethylsilane / dichloromethane 3: potassium carbonate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 1,4-dioxane; lithium hydroxide monohydrate / 4 h / 100 °C / Inert atmosphere | ||
| Multi-step reaction with 3 steps 1: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate); lithium hydroxide monohydrate / acetonitrile / 30 °C 2: methanesulfonic acid; triethylsilane / dichloromethane 3: potassium carbonate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 1,4-dioxane; lithium hydroxide monohydrate / 4 h / 100 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) / lithium hydroxide monohydrate; acetonitrile / 30 °C 2: methanesulfonic acid; triethylsilane / dichloromethane 3: potassium carbonate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 1,4-dioxane; lithium hydroxide monohydrate / 4 h / 100 °C / Inert atmosphere | ||
| Multi-step reaction with 3 steps 1: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate); lithium hydroxide monohydrate / acetonitrile / 30 °C 2: methanesulfonic acid; triethylsilane / dichloromethane 3: potassium carbonate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 1,4-dioxane; lithium hydroxide monohydrate / 4 h / 100 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 4 steps 1: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) / lithium hydroxide monohydrate; acetonitrile / 30 °C 2: methanesulfonic acid; triethylsilane / dichloromethane 3: potassium carbonate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 1,4-dioxane; lithium hydroxide monohydrate / 4 h / 100 °C / Inert atmosphere 4: ammonium carbamate; [bis(acetoxy)iodo]benzene / methanol / 5 h / 25 °C | ||
| Multi-step reaction with 4 steps 1: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate); lithium hydroxide monohydrate / acetonitrile / 30 °C 2: methanesulfonic acid; triethylsilane / dichloromethane 3: potassium carbonate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 1,4-dioxane; lithium hydroxide monohydrate / 4 h / 100 °C / Inert atmosphere 4: ammonium carbamate; [bis(acetoxy)iodo]benzene / methanol / 5 h / 25 °C |