Structure of 77395-10-9
*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 !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
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) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
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) ]}
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
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
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. : | 77395-10-9 |
Formula : | C9H6BrNO2 |
M.W : | 240.05 |
SMILES Code : | O=C1NC2=C(C=C(Br)C=C2C)C1=O |
MDL No. : | MFCD00463080 |
InChI Key : | NPRAKNSGKOICIE-UHFFFAOYSA-N |
Pubchem ID : | 542843 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
77% | With bromine; In chloroform; at 20 - 80℃; for 24.25h; | Step 3: 5-bromo-7-methylindoline-2,3-dioneTo a stirred mixture of 7-methylindoline-2,3-dione (7 g, 0.043 mol) in chloroform (700 mL) was added a solution of bromine (2.8 mL, 0.053 mol) in chloroform (100 mL) dropwise over 15 min at room temperature. The reaction mixture was heated at 80C for 24 h and then cooled to 0C, which resulted in precipitation of the product as a red solid. The solid was collected by suction filtration and dried under vacuum to afford the title compound (8 g, 77%).XH NMR (400 MHz, DMSO-d6) : δ 11.20 (s, 1H), 7.64 (d, J = 1.2 Hz, 1H), 7.42 (d, J = 7.2 Hz, 1H), 2.18 (s, 3H); ESI-MS: Calculated mass: 238.96; Observed mass: 238.30 [M-H]". |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With dihydrogen peroxide; sodium chloride; sodium hydroxide; In water; at 0℃; for 1.5h; | Step 4: 2-amino-5-bromo-3-methylbenzoic acidA mixture of <strong>[77395-10-9]5-bromo-7-methylindoline-2,3-dione</strong> (8 g, 0.033 mol), sodium chloride (4.5 g, 0.09 mol) and sodium hydroxide (3.6 g, 0.09 mol) was dissolved in water (96 mL) with stirring to give a yellow solution. The reaction mixture was cooled to 0C and to this mixture was added slowly a solution of 30% hydrogen peroxide (7 mL) and .sodium hydroxide (6.27 g) in 83 mL of water. The reaction mixture was stirred for another 1.5 h at 0C and then quenched with glacial acetic acid to give a tan precipitate. The solid was filtered, washed thoroughly with cold water and dried under vacuum to afford the title compound (5.8 g, 75%).XH NMR (400 MHz, DMSO-d6) : δ 7.69 (d, J = 2.4 Hz, 1H), 7.26 (s, 1H), 2.0 (s, 3H); ESI-MS : Calculated mass: 228.97; Observed mass: 228.10 [M-H] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sulfuric acid; at 80℃; for 2h; | To a 250-mL round-bottom flask was placed a solution of N-(4-bromo-2-methylphenyl)-2-(N-hydroxyimino)acetamide (7.38 g,28.71 mmol,as prepared in the previous step) in concentrated H2504 (70 mL). The solution was stirred for 2 h at 80C then quenched by the addition of 500 mL of water/ice. The precipitate was isolated by filtration,washed with water (3x200 mL),anddried affording 6.5 g (94%) of the title compound as a red solid. Mass Spectrum (LCMS,ESI pos): Calcd. for C9H7BrNO2: 240.0 (M+H); Found: 240.0. 1H NMR (400 MHz,DMSO-d6): ö 11.16 (s,1H ),7.60 (s,1H ),7.44 (s,1H ),2.14 (s,3H). |
6.65 g | With sulfuric acid; at -5 - 80℃; | 4-Bromo-2-methylaniline 18 (6.88 g, 37 mmol) was added to a 500 mL flask and was reacted with chloral hydrate (7.35 g, 44.4 mmol), hydroxylamine hydrochloride (9.25 g, 133 mmol), sodium sulfate (42 g, 295 mmol) in water (250 mL) and 2 M HCl (12.5 mL), by heating the mixture at 55 C with vigorous stirring for 14 h. After cooling to room temperature, the aqueous layer was decanted from the formed gummy residue which was further washed with cold water and dried under vacuum. The flask was then cooled to -5 - 0 C using ice/salt bath before adding cold sulfuric acid (22.5 mL). The flask was allowed to warm to room temperature before heating the reaction mixture gradually to 70 C where the mixture started to get darker in colour. When the colour change became stable after almost 30 min, the reaction was heated to 80 C for 10 min. After cooling to room temperature, the mixture was poured onto crushed ice (150 mL) and stirred for 1 h. The separated solid was then filtered and washed with water (3 * 100 mL) to give a red solid of 5-bromo-7-methylindoline-2,3-dione 20 (6.65 g, 75%) and was sufficiently pure for the next step. The spectral data were consistent with the reported literature. 44 |
2.7 g | With sulfuric acid; In 1,2-dichloro-ethane; at 0 - 25℃; for 16h; | To a stirred mixture of ethylene dichloride (12 g) and sulphuric acid (8.2 g, 84 mmol), N-(4-bromo-2- methylphenyl)-2-(hydroxyimino)acetamide (3 g, 12 mmol) was added portion-wise at 0-10 C. The reaction mixture was stirred at 20-25 C for 16 h. After completion of the reaction, the reaction mixture was quenched by addition of ice cold water (30 g). The reaction mass was further heated to 45-50 C under stirring for 1 h. The precipitate obtained was filtered and dried under reduced pressure to obtain 5-bromo-7-methylindoline-2,3-dione (2.7 g, 11 mmol 1H-NMR (DMSO-d6, 400 MHz): 11.17 (s, 1H), 7.53 (d, J = 7.6 Hz, 1H), 7.19 (d, J = 7.6 Hz, 1H), 2.19 (s, 3H). MS: m/z = 241 [M+H] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 107A 6-Bromo-3,8-dimethyl-2-phenylquinoline-4-carboxylic acid (0758) (0759) 3.00 g (12.50 mmol) of 364 <strong>[77395-10-9]5-bromo-7-methyl-1H-indole-2,3-dione</strong> were initially charged in 34 ml of 41 acetic acid, and 1.68 g (12.50 mmol) of 40 1-phenylpropan-1-one were added. The reaction mixture was stirred at 75 C. for 5 min. Subsequently, 11 ml of 42 conc. hydrochloric acid were added, and stirring of the mixture was continued at 115 C. overnight. After cooling to RT, the reaction mixture was added to 200 ml of 1 M hydrochloric acid. The precipitated solids were filtered off, washed twice with 10 ml of 43 water and dried under reduced pressure. 3.02 g (64% of theory, 94% purity) of the 365 title compound were obtained. (0760) 1H-NMR (400 MHz, DMSO-d6): [ppm]=14.31 (br. s, 1H), 7.83 (s, 1H), 7.77-7.63 (m, 3H), 7.57-7.49 (m, 3H), 2.70 (s, 3H), 2.41 (s, 3H). (0761) LC/MS (Method 1, ESIpos): Rt=1.15 min, m/z=356/358 [M+H]+. | ||
3.00 g (12.50 mmol) of <strong>[77395-10-9]5-bromo-7-methyl-1H-indole-2,3-dione</strong> were initially charged in 34 ml of acetic acid, and 1.68 g (12.50 mmol) of 1-phenylpropan-1-one were added. The reaction mixture was stirred at 75 C. for 5 min. Subsequently, 11 ml of conc. hydrochloric acid were added, and stirring of the mixture was continued at 115 C. overnight. After cooling to RT, the reaction mixture was added to 200 ml of 1 M hydrochloric acid, and the precipitated solid was filtered off, twice washed with 10 ml of water and dried under reduced pressure. This gave 3.02 g (64% of theory; purity 94%) of the title compound. 1H-NMR (400 Mhz, DMSO-d6): δ [ppm]=14.31 (br. s, 1H), 7.83 (s, 1H), 7.77-7.63 (m, 3H), 7.57-7.49 (m, 3H), 2.70 (s, 3H), 2.41 (s, 3H). LC/MS (Method 1, ESIpos): Rt=1.15 min, m/z=356/358 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With triethylamine; In N,N-dimethyl-formamide; at 70℃; for 2.5h; | General procedure: 0.31 g (1.1 mmol) of 3,5-di-tert-butyl-4-hydroxybenzyl acetate 14 and 0.03 mL of triethyl-amine were added to a continuously stirred solution of the isatin derivative 1-13 (1 mmol) in DMF. The reaction was performed at 70, completion of the reaction of the reactants was determined by TLC. After cooling to ambient, the reaction mixture was poured into a brine. The obtained precipitate was filtered off, washed with water, and dried in vacuum (12 mmHg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; at 85℃; for 4h;Inert atmosphere; Sealed tube; | General procedure: Under a N2 atmosphere, a 25 mL flask was charged with the 5-bromoisatin derivative (1 equiv), 3-(3-boronophenyl)propanoicacid 27 (1.2 equiv), tetrakis(triphenylphosphine)palladium(0)(5 mol%) and DME (3 mL) or diglyme (3 mL), was sealed with arubber cap. The reaction mixture was degassed by flushing N2through a needle for 10 min, and was then heated in an oil bath at85 C. When the solid dissolved, a N2 degassed solution of potassiumphosphate (3 equiv) inwater (3 mL) was added to the reactionmixture and heating continued at 85 C for 4e6 h. After cooling toroom temperature, the solvent was concentrated under reducedpressure. A solution of HCl 2 M (15 mL) was added, and theresulting suspended solid was either collected by filtration orextracted with ethyl acetate (2 25 mL). The combined organiclayers were dried (MgSO4) and evaporated under reduced pressure.The combined residues were then dissolved in ethanol and weresubjected to PLC (10% methanol in CH2Cl2, 0.5% acetic acid) to yieldthe isatin-acid conjugates 34e37.2.5.4.2 3-(3-(7-Methyl-2,3-dioxoindolin-5-yl)phenyl)propanoic acid (35) Following the general procedure 3 using <strong>[77395-10-9]5-bromo-7-methylindoline-2,3-dione</strong> 20 (100 mg, 0.416 mmol), 3-(3-boronophenyl)propanoic acid 27 (96.8 mg, 0.499 mmol), tetrakis(triphenylphosphine)palladium(0) (24 mg, 0.021 mmol) and potassium phosphate (264.9 mg, 1.248 mmol) and heating for 4 h, the acid 35 was isolated as a red solid (70 mg, 55%), mp: 238-239 C; IR (cm-1): ν 3172 (m, NH), 2989 (m, OH), 1731 (s, C=O), 1696 (s, C=O). 1H NMR (acetone-d6), δ: 9.94 (s, NH), 7.81 (s, 1H, isatin_4 H), 7.66 (s, 1H, phenyl_2 H), 7.60 (s, 1H, isatin_6 H), 7.50 (d, J = 7.6 Hz, 1H, pheny_6 H), 7.40 (t, J = 7.6 Hz, 1H, phenyl_5 H), 7.29 (d, J = 7.6 Hz, 1H, phenyl_4 H), 3.03 (t, J = 7.3 Hz, 2H, COOH-CH2-CH2), 2.71 (t, J = 7.3 Hz, 2H, COOH-CH2-CH2), 2.41 (s, 3H, CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In diethylene glycol dimethyl ether; water; at 85℃; for 5h;Inert atmosphere; Sealed tube; | General procedure: Under a N2 atmosphere, a 25 mL flask was charged with the 5-bromoisatin derivative (1 equiv), (3-(cyanomethoxy)phenyl)boronic acid 39 (1 equiv), tetrakis(triphenylphosphine)palladium(0) (5 mol%), potassium phosphate (3 equiv) and a mixture of diglyme (3 mL) and water (3 mL), and the reaction mixture was degassed by flushing N2 through a needle for 10 min. The flask was then sealed and heated at 85 C for 5-9 h. After cooling to room temperature, the solvent was concentrated under reduced pressure, and 1 N HCl (15 mL) was added. The suspended solid was either collected by filtration or extracted with ethyl acetate (2 * 25 mL). The combined organic layers were dried (MgSO4) and evaporated under reduced pressure. The combined residues were adsorbed onto silica and subjected to flash column chromatography (40% ethyl acetate in petroleum spirit) to yield the acetonitrile derivatives.2.5.12.2 2-(3-(7-Methyl-2,3-dioxoindolin-5-yl)phenoxy)acetonitrile (53) Following the general procedure 7 using <strong>[77395-10-9]5-bromo-7-methylindoline-2,3-dione</strong> 20 (100 mg, 0.416 mmol), (3-(cyanomethoxy)phenyl)boronic acid 39 (73.6 mg, 0.416 mmol), tetrakis(triphenylphosphine)palladium(0) (24 mg, 0.021 mmol), potassium phosphate (264.9 mg, 1.248 mmol) and heating for 5 h, the acetonitrile intermediate 53 was isolated as a red solid (63.2 mg, 52%), mp: 208-209 C; IR (cm-1): ν 3185 (w, NH), 2365 (m, CN), 1750 (s, C=O), 1587 (s, C=O). 1H NMR (acetone-d6), δ: 10.13 (s, NH), 7.83 (s, 1H, isatin_4 H), 7.68 (s, 1H, isatin_C6), 7.47 (t, J = 7.8 Hz, 1H, phenoxy_5 H), 7.40-7.38 (m, 2H, phenoxy_2,4 H), 7.09 (d, J = 8.0 Hz, 1H, phenoxy_6 H), 5.21 (s, 2H, CH2), 2.39 (s, 3H, CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With titanium tetrachloride; zinc; In tetrahydrofuran; at 20℃; for 18h;Inert atmosphere; | To a suspension of zinc dust (3.3 g, 51 mmol) in dry THF (60 mE) was added titanium tetrachioride (2.8 mE, 26 mmol) dropwise at rt under argon. The reaction mixture was heated to reflux for 2 h and then allowed to cool it. To this mixture was added 5-bromo-7-methylindoline-2,3-di- one (2.0 g, 8.3 mmol) in dry THF (40 mE) in portions. The reaction mixture was stirred at it for 18 h. The reaction was quenched with 1 M HC1 (40 mE). The mixture was diluted with EtOAc (60 mE) and the layers were separated. The organic layer was washed with brine (1 x20 mE), dried over Mg504, filtered, and evaporated. The residue was purified by flash column chromatography (5i02 10% EtOAc/ CHC13). The product was then triturated with diisopropyl ether (10 mE) to give the title compound (1.0 g, 53% yield) as a pink crystalline solid. MS (ESI): mass calcd. for C9H8I3rNO, 225.0; m/z found, 224.0 [M-H]. |
A263853 [34921-60-3]
5-Bromo-7-ethylindoline-2,3-dione
Similarity: 1.00
A342544 [849630-82-6]
5-Bromo-7-isopropylindoline-2,3-dione
Similarity: 0.97
A263853 [34921-60-3]
5-Bromo-7-ethylindoline-2,3-dione
Similarity: 1.00
A342544 [849630-82-6]
5-Bromo-7-isopropylindoline-2,3-dione
Similarity: 0.97
A263853 [34921-60-3]
5-Bromo-7-ethylindoline-2,3-dione
Similarity: 1.00
A342544 [849630-82-6]
5-Bromo-7-isopropylindoline-2,3-dione
Similarity: 0.97
A263853 [34921-60-3]
5-Bromo-7-ethylindoline-2,3-dione
Similarity: 1.00
A342544 [849630-82-6]
5-Bromo-7-isopropylindoline-2,3-dione
Similarity: 0.97