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CAS No. : | 2058-72-2 | MDL No. : | MFCD00456313 |
Formula : | C9H6BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GEEDYJPPYNIZLX-UHFFFAOYSA-N |
M.W : | 240.05 | Pubchem ID : | 16357 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 54.76 |
TPSA : | 37.38 Ų |
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) : | -6.86 cm/s |
Log Po/w (iLOGP) : | 1.62 |
Log Po/w (XLOGP3) : | 1.27 |
Log Po/w (WLOGP) : | 1.23 |
Log Po/w (MLOGP) : | 1.2 |
Log Po/w (SILICOS-IT) : | 2.06 |
Consensus Log Po/w : | 1.48 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.47 |
Solubility : | 0.813 mg/ml ; 0.00339 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.65 |
Solubility : | 5.32 mg/ml ; 0.0222 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.31 |
Solubility : | 0.118 mg/ml ; 0.000492 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.78 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
70% | General procedure: Isatin or 5-substituted isatin (7 mmol) and K2CO3 (10 mmol) were added to a dry CH3CN solution (25 mL) and stirred for 30 min at RT. Methyl iodide or benzyl chloride (7.5 mmol) was added to the solution and then refluxed at 80C for 3 hour. The mixture was cooled to RT and the solvent was removed. The residue was dissolved in CH2Cl2(30 mL) and then washed with H2O (3x30 mL). The organic extracts were dried over anh Na2SO4 and concentrated to give the crude brown solid. The purification of the crude solid using flash-column chromatography (silica gel, hexane/EtOAc (2:1) gave the pure compounds 3a-g. | |
General procedure: Isatins I (3.0 mmol) was dissolved in anhydrous DMF (15 mL), and the resultant solution was cooled to 0 C (ice bath), whereupon sodium hydride (60% dispersion in mineral oil, 140mg, 3.5 mmol, 1.17 equiv) was added in one portion and stirred for 5 minutes. Iodomethane (497 mg, 3.5 mmol, 1.17 equiv) or benzyl bromide (564.3 mg, 3.3 mmol, 1.1 equiv) was added and the reaction was stirred at 0 C for 30min. The reaction was monitored by TLC until I was fully consumed. The reaction mixture was then poured into saturated aqueous NH4Cl and extracted with ethyl acetate. The combined organic portions were washed with water and brine, dried (MgSO4), filtered, and concentrated to give N-methyl isatins and N-benzyl isatins II (90%-100% yield). | ||
With sodium hydride; In N,N-dimethyl-formamide; at 0℃; | General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2·NH2-H2O ( 35 %) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid. |
With potassium carbonate; potassium iodide; for 3h;Reflux; | General procedure: Isatin derivatives 1a-c (0.005 mol) were stirred in acetonitrile(20 mL) with (0.007 mol) of the appropriate methyl iodide 2, propyliodide 3 or benzyl bromide 7a-d in the presence of catalytic amountof potassium iodide with (0.010 mol) of dry potassium carbonate atreflux temperature. The reaction was monitored with TLC. Aftercomplete of reaction, the mixture was poured into ice-water, theformed solid was collected, washed with water and recrystallizedfrom ethanol-water to furnish the final compounds 4a-f and 8a-l[58-61]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a sol. of 5-bromo-1-methyl-1 H-indole- 2,3-dione (3.60 g, 15.0 mmol) in THF (100 mL) are added sequentially at rt trifluoromethyl)trimethylsilane (4.43 mL, 30.0 mmol) and CsF (91.1 mg, 0.60 mmol). The resulting sol. is stirred at rt overnight. The mixture is quenched with cold water (100 mL). The mixture is extracted with EtOAc (3 x 100 mL). The comb. org. layers are washed with brine (100 mL), dried over MgS04, filtered, and the solvents are removed under reduced pressure. Purification of the residue by automated FC (Combiflash, column 80 g, flow 60 mL/min, EtOAc / heptane 0:100 ? 20:80) yields the tri methyl si lyl -protected product. To a sol. of this isolated compound in MeOH (50 mL) is added aq. 2M HCI (40 mL). The resulting sol. is stirred at rt for 2 h. The reaction is diluted with CH2CI2 (100 mL). The layers are separated and the aq. phase is extracted with CH2CI2 (2x 50 mL). The comb. org. layers are washed with brine (1 x 50 mL), dried over MgS04, filtered, and the solvents are removed under reduced pressure to yield the crude title product. LC-MS: tR = 0.79 min (conditions 3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With tert.-butylnitrite; oxygen; In tetrahydrofuran; at 50℃; under 760.051 Torr; for 24h;Schlenk technique; Inert atmosphere; | General procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In a similar manner to d), the following 1-alkyl- or 1-benzyl-1H-indole-2,3-diones were prepared. 5,7-dinitro-1-ethyl-1H-indole-2,3-dione, M.p. 135-140 C. 5-bromo-1-methyl-1H-indole-2,3-dione, M.p. 157-160 C. | ||
In a similar manner to d), the following 1-alkyl or 1-benzyl-1H-indole-2,3-diones were prepared. 5,7dinitro-1-ethyl-1H-indole-2,3-dione, m.p. 135 to 140 C. 5-bromo-1-methyl-1H-indole-2,3-dione, m.p. 157 to 160 C. | ||
In a similar manner to d), the following 1-alkyl- or 1-benzyl-1H-indole-2,3-diones were prepared. 5,7-dinitro-1-ethyl-1H-indole-2,3-dione, M.p. 135-140 C. 5-bromo-1-methyl-1H-indole-2,3-dione, M.p. 157-160 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With zinc(II) oxide; at 100℃; for 2h; | General procedure: Isatin (1 mmol), dimedone (280 mg, 2 mmol) and ZnO (0.25 mmol) were taken in the round bottom flask and heated to 100 C for 2 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was suspended in 6 mL (3:3 v/v) chloroform and methanol mixture and the catalyst was filtered through Whatman filter paper. The filtrate was concentrated under reduced pressure and the residue was purified by recrystallization in ethanol solvent. The recovered catalyst dried and used for next cycle. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With C3H6N6*3C5H9NO2; In dimethyl sulfoxide; at 20℃; | General procedure: To a solution of L-proline-melamine complex (3 mol%) in DMSO (2 mL) was added dimedone 0.025 mg (0.178 mmol), malononitrile (1 equiv) and benzaldehyde / isatin (1 equiv) and stirred at room temperature for 1-20 min. After completion of the reaction (monitored by TLC), ethyl acetate was added stirring and continued for another 5 min. The precipitate formed was filtered. Evaporation of solvent gave the crude product which was recrystallized using ethanol to give the pure compound. |
Tags: 2058-72-2 synthesis path| 2058-72-2 SDS| 2058-72-2 COA| 2058-72-2 purity| 2058-72-2 application| 2058-72-2 NMR| 2058-72-2 COA| 2058-72-2 structure
[ 34921-60-3 ]
5-Bromo-7-ethylindoline-2,3-dione
Similarity: 0.94
[ 34921-60-3 ]
5-Bromo-7-ethylindoline-2,3-dione
Similarity: 0.94
[ 34921-60-3 ]
5-Bromo-7-ethylindoline-2,3-dione
Similarity: 0.94
[ 34921-60-3 ]
5-Bromo-7-ethylindoline-2,3-dione
Similarity: 0.94
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