Structure of 675605-92-2
*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. : | 675605-92-2 |
| Formula : | C14H21BO3 |
| M.W : | 248.13 |
| SMILES Code : | CC1(C)C(C)(C)OB(C2=CC=C(COC)C=C2)O1 |
| English Name : | 2-(4-(Methoxymethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
| MDL No. : | MFCD18733409 |
| InChI Key : | AYKXQFSQDGLWAB-UHFFFAOYSA-N |
| Pubchem ID : | 59882226 |
* 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 |
|---|---|---|
| 25% | With barium dihydroxide; tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 90℃; for 12h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / ethanol / 0.5 h / 80 °C 2: water; sodium hydroxide / tetrahydrofuran; ethanol / 1 h / 80 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / ethanol / 0.5 h / 80 °C 2: water; sodium hydroxide / tetrahydrofuran; ethanol / 1 h / 80 °C 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 80 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / ethanol / 0.5 h / 80 °C 2: water; sodium hydroxide / tetrahydrofuran; ethanol / 1 h / 80 °C 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 80 °C 4: hydroxylamine; water / tetrahydrofuran; ethanol / 2 h / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In ethanol at 80℃; for 0.5h; | 3.2 Example 3 (2) Ethyl 4-iodobenzoate (5.5 g), tetrakis(triphenylphosphine)palladium (1.2 g), and cesium carbonate (9.8 g) were added to an ethanol (0.10 L) solution of 2-[4-(methoxymethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.1 g), as obtained in Example 3-(1). The mixture was stirred for 30 minutes at 80°C, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel chromatography (hexane/ethyl acetate = 85/15) to obtain ethyl 4'-(methoxymethyl)biphenyl-4-carboxylate (light yellow solid) (3.5 g, 80%). MS (ESI/APCI Dual): 271 (M+H)+ 1H NMR (200 MHz, CHLOROFORM-d) δ ppm 1.43 (3 H, t, J=7.0 Hz), 3.43 (3 H, s), 4.42 (2 H, q, J=7.0 Hz), 4.51 (2 H, s), 7.41 - 7.45 (2 H, m), 7.57 - 7.70 (4 H, m), 8.06 - 8.15 (2 H, m) |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 82% | Stage #1: sodium methylate; 1-bromomethyl-4-bromobenzene In methanol at 20℃; for 21h; Stage #2: bis(pinacol)diborane With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 100℃; for 4h; | 3.1 Example 3 (1) A 28% sodium methoxide-methanol solution (5.0 g) was added to a methanol (40 mL) solution of 1-bromo-4-(bromomethyl)benzene (5.0 g) at room temperature, and the mixture was stirred for 21 hours at room temperature. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether, whereafter the organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered out, and the filtrate was concentrated under reduced pressure. To a DMSO solution (40 mL) of the resulting residue, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane (7.6 g), PdCL2(dppf) · CH2Cl2 (0.82 g), and potassium acetate (5.9 g) were added, followed by stirring the mixture for 4 hours at 100°C. After the system was allowed to cool, water (0.10 L) and ethyl acetate (0.10 L) were added, and the precipitated insolubles were filtered out. The filtrate was extracted with ethyl acetate, and the organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The desiccant was filtered out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/ethyl acetate = 90/10 → 80/20) to obtain 2-[4-(methoxymethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (light green solid) (4.1 g, 82%). MS (ESI): 249 (M+H)+ 1H NMR (200 MHz, CHLOROFORM-d) δ ppm 1.34 (12 H, s), 3.38 (3 H, s), 4.48 (2 H, s), 7.30 - 7.38 (2 H, m), 7.76 - 7.83 (2 H, m) |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 35% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos In 1,4-dioxane at 140℃; for 16h; | 151 To a stirred and cooled (0 °C) suspension of 2,4-dichloro-l,3,5-triazine (0.800 g, 5.33 mmol) and potassium carbonate (1.47 g, 10.7 mmol)in tetrahydrofuran (20 mL) was added, dropwise over 30 minutes, a solution of tert-butyl 3-isopropylpiperazine-l- carboxylate (1.22 mg, 5.33 mmol) in tetrahydrofuran (10 mL). The mixture was stirred at 0 °C for 2 hours and then at room temperature overnight. The reaction was then concentrated and the residue was purified by column chromatography over neutral alumina using a hexane/ethyl acetate eluant to afford tert-butyl 4-(4-chloro-l,3,5-triazin- 2-yl)-3-isopropylpiperazine-l -carboxylate as a white solid (1.10 g, 60%). To a stirred solution of this intermediate a (0.450 g, 1.32 mmol) in 1,4-dioxane was added 2-(4-((2- methoxyethoxy)methyl)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (0.391 g, 1.58 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.119 g, 0.130 mmol), 2- dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.124 g, 0.260 mmol) and cesium carbonate (1.08 g, 3.31 mmol). The mixture was heated overnight at 140 °C for 16 hours, filtered through Celite, and concentrated. The residue was purified by flash chromatography over silica gel using a dichloromethane/methanol eluant to afford tert- butyl 3-isopropyl-4-(4-(4-(methoxymethyl)phenyl)-l,3,5-triazin-2-yl)piperazine-l- carboxylate as a white solid (200 mg, 35%>). To a stirred and cooled (0 °C) solution of this intermediate (200 mg, 0.470 mmol) in dichloromethane (10 mL) was added trifluoracetic acid (10 mL). The reaction was stirred for another 3 hours at 0 °C before diluting with 2.0 N aqueous potassium carbonate solution (enough to render the mixture basic) and extracting with dichloromethane. The combined organic phases were washed with brine, dried (Na2S04) and concentrated to afford 2-(2-isopropylpiperazin-l-yl)-4-(4- (methoxymethyl)phenyl)-l,3,5-triazine as a white solid (150 mg, crude). Using General Procedure A and Intermediate 5, this intermediate was used to generate the title compound as a light yellow solid (0.040 g, 15%). 1H NMR (500 MHz, CDC13) δ 8.65 (d, J= 3.0 Hz, 1H), 8.41-8.37 (m, 2H), 7.47-7.45 (m, 2H), 4.99 (m, 0.5H), 4.80 (m, 1H), 4.63 (m, 0.5H), 4.56 (s, 2H), 4.35 (d, J = 12.5 Hz, 1H), 4.08-3.89 (m, 2H), 3.44 (s, 3H), 3.19- 2.84 (m, 9H), 2.42-2.40 (m, 1H), 2.24 (m, 1H), 1.98-1.56 (m, 9H), 1.19-1.13 (m, 3H), 0.89-0.85 (m, 3H) ppm. 13C NMR (125 MHz, CDC13) δ 170.5, 170.2, 166.2, 166.0, 164.5, 156.8, 142.5, 135.6, 135.5, 128.6, 128.5, 127.5, 74.2, 59.2, 59.1, 58.3, 56.8, 56.7, 56.6, 53.1, 47.6, 47.5, 46.4, 46.2, 44.5, 44.1, 44.0, 43.6, 43.5, 43.4, 43.3, 39.8, 39.6, 38.6, 38.4, 36.6, 36.4, 27.0, 26.6, 26.5, 25.8, 25.6, 24.3, 24.0, 20.5, 20.4, 20.3, 20.2, 19.0, 18.7 ppm. Purity: > 95% LCMS (214 nm & 254 nm); retention time 1.90 min; (M+H+) 508.3. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 61% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; Inert atmosphere; | 119.A To a solution of 1 -bromo-4-(methoxymethyl)benzene (500 mg, 2.487 mmol) in 1 ,4- dioxane (50 mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1 ,3,2-dioxaborolane) (947 mg, 3.73 mmol), PdCl2(dppf)-CH2Cl2 adduct (203 mg, 0.249 mmol) and potassium acetate (488 mg, 4.97 mmol). The reaction mixture was heated to 100 °C under N2 and stirred overnight. The mixture was evaporated, water (50 mL) was added, and the aqueous layer was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over Na2S04 and concentrated. The residue was purified with silica gel chromatography (ethyl acetate/petroleum ether: 0-1/40) to afford 2-(4- (methoxymethyl)phenyl)-4,4, 5, 5-tetramethyl-1 ,3,2-dioxaborolane (420 mg, 1 .523 mmol, 61 % yield) as a colourless oil. |
| 42 % | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere; | 8 Preparation 42: 2-(4-(methoxymethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2- dioxaborolane To a mixture of 1-bromo-4-(methoxymethyl) benzene (3.00 g, 14.9 mmol, 1.00 equiv) and bis(pinacolato)diboron (7.58 g, 29.8 mmol, 2.00 equiv) in 1,4-dioxane (40 mL) was added Pd(dppf)Cl2·CH2Cl2 (1.09 g, 1.49 mmol, 0.100 equiv) and KOAc (2.93 g, 29.8 mmol, 2.00 equiv) at room temperature under a nitrogen atmosphere. The resulting mixture was stirred overnight at 80 °C. The reaction was quenched with water. The resulting mixture was extracted with EtOAc (5 x 50 mL). The combined organic layers were washed with brine (3 x 50 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with EA / MeOH (10:1) to afford the crude product (2.30 g, crude) and further purified by Prep-HPLCO to afford the title compound as a yellow oil (1.56 g, 42%) |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / acetonitrile; water / 2 h / 80 °C / Inert atmosphere 2: hydrogenchloride / dichloromethane; methanol / 2 h / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 55% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In water; acetonitrile at 80℃; for 2h; Inert atmosphere; | 119.B To a solution of (2R)-4-(5-bromo-4-fluoro-1 -oxoisoindolin-2-yl)-2-methyl-2- (methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yl)oxy)butanamide (Intermediate 16) (654 mg, 1 .29 mmol) in acetonitrile (6 mL) and water (1 mL) was added 2-(4- (methoxymethyl)phenyl)-4,4,5,5-tetramethyl-1 ,3,2- dioxaborolane (400 mg, 1 .612 mmol), PdCl2(dppf)-CH2Cl2 adduct (132 mg, 0.161 mmol) and K2C03 (446 mg, 3.22 mmol) under nitrogen. The mixture was heated to 80 °C for 2 hr. The mixture was concentrated, water (20 mL) was added and the aqueous layer was extracted with ethyl acetate (20 mL x 3), dired over Na2S04, and evaporated. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether: 1 /2-2/1) to afford (2R)-4-(4-fluoro-5-(4-(methoxymethyl)phenyl)-1 -oxoisoindolin-2-yl)-2-methyl-2- (methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yl)oxy)butanamide (500 mg, 0.880 mmol, 55 % yield) as a yellow solid. LCMS: [M+H] 572.3. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 78% | With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene In tetrahydrofuran; water at 60℃; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate In 1,4-dioxane; water at 80℃; for 16h; Inert atmosphere; | 4-[2-Amino-4-ethyl-5-(1H-indazol-5-yl)-3-pyridyl]phenol (GNE-6640) General procedure: into a 250-ml three-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed 4-(2-amino-5-bromo-4-ethylpyridin-3-yl)phenol (1.0 g, 3.41 mmol), 6-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole (880 mg, 3.41 mmol,), potassium carbonate (3.3 g, 23.88 mmol), water (30 ml), 1,4-dioxane (25 ml), and Pd(dppf)Cl2 (200 mg, 0.3 mmol). The resulting solution was stirred at 80 °C for 16 h, and diluted with 500 ml H2O and 500 ml ethylacetate.The organic layer was washed twice with brine (2 × 250 ml) and concentrated under vacuum. The residue was purified on a silica gel column eluting with DCM/CH3OH (20:1-10:1) to afford the title compound. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 88% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 13h; Inert atmosphere; | 16.16-1 Synthesis Example 16-1 Under a nitrogen atmosphere, 3-benzyl-5-bromopyrazine-2-amine (166.0 mg, 0.6 mmol, 1 eq.) and 2-(4-(methoxymethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (249.5 mg, 1.0 mmol, 1.6 eq.) were dissolved in ethanol (2 ml) and toluene (12 ml). To the solution was added 1 M aqueous sodium carbonate solution (3 ml) and the mixture was stirred at room temperature. The reaction solution was degassed under vacuum. To the solution was added a catalytic amount of tetrakis(triphenylphosphine)palladium (0) (about 1 cup of micro spatula) and the mixture was degassed again under vacuum and then stirred at 100° C. overnight (13 hours). After allowing the mixture to cool to room temperature, the mixture was filtered through Celite to remove palladium catalyst. The resulting residue was extracted with ethyl acetate, washed with distilled water and saturated brine, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (eluent: hexane/ethyl acetate=1/2→1/1) to obtain 3-benzyl-5-(4-(methoxymethyl)phenyl)pyrazine-2-amine as a yellow solid (169.5 mg, 0.5 mmol, 88%). 1H-NMR (500 MHz, CDCl3): δ (ppm)=8.39 (s, 1H), 7.93 (d, J=8.3 Hz, 2H), 7.42 (d, J=8.3 Hz, 2H), 7.43-7.25 (m, 5H), 4.51 (s, 2H), 4.42 (s, 2H), 4.19 (s, 2H), 3.4 (s, 2H). 13C-NMR (150 MHz, CDCl3): δ (ppm)=41.42, 58.18, 74.53, 76.90, 77.16, 77.41, 125.91, 127.21, 128.33, 128.71, 129.13, 136.85, 137.65, 138.17, 140.74, 142.51, 151.88. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 13 h / 100 °C / Inert atmosphere 2: hydrogenchloride / ethanol; water / 4 h / 0 - 80 °C / Inert atmosphere |