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CAS No. : | 860624-88-0 | MDL No. : | MFCD11845501 |
Formula : | C10H10BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AXFDCMFCJPYARR-UHFFFAOYSA-N |
M.W : | 256.10 | Pubchem ID : | 49758858 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 60.51 |
TPSA : | 38.33 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) : | -6.1 cm/s |
Log Po/w (iLOGP) : | 2.46 |
Log Po/w (XLOGP3) : | 2.48 |
Log Po/w (WLOGP) : | 1.63 |
Log Po/w (MLOGP) : | 2.25 |
Log Po/w (SILICOS-IT) : | 2.66 |
Consensus Log Po/w : | 2.3 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.18 |
Solubility : | 0.171 mg/ml ; 0.000668 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.93 |
Solubility : | 0.301 mg/ml ; 0.00118 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.93 |
Solubility : | 0.0299 mg/ml ; 0.000117 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.97 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-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 |
---|---|---|
100% | at 20℃; for 16 h; | 1-(1 ,1-dimethylethyl) 7-methyl 5-bromo-2,3-dihydro-1 H-indole-1 , 7-dicarboxylate (9 g, 25 mmol) was dissolved in trifluoroacetic acid (6 ml.) and stirred at room temperature for 16 hours. Dichloromethane and sodium hydroxide solution (2 M) were added and the organic layer washed twice with sodium hydroxide solution until the aqueous layer pH > 7. The organic layer was then concentrated in vacuo to give 6.5 g (100percent) of the title compound as a brown solid.1 H NMR (400 MHz, DMSO-D6) δ ppm 2.99 (t, J=8.5 Hz, 2 H) 3.61 (t, J=8.4 Hz, 2 H) 3.78 (s, 3 H) 6.72 (s, 1 H) 7.28 (d, J=1 Hz, 1 H) 7.46 (d, J=2 Hz, 1 H); MS m/z 256/258 (1 :1 ratio) (M+1)+ Rt 3.32 min. |
100% | at 20℃; for 16 h; Inert atmosphere | Intermediate 7:Methyl 5-bromo-2,3-dihydro-1 H-indole-7-carboxylate.1 -(1 ,1 -dimethylethyl) 7-methyl 5-bromo-2,3-dihydro-1 H-indole-1 , 7-dicarboxylate (9 g, 25 mmol) was dissolved in trifluoroacetic acid (6 ml.) and stirred at room temperature for 16 hours. Dichloromethane and sodium hydroxide solution (2 M) were added and the organic layer washed twice with sodium hydroxide solution until the aqueous layer pH > 7. The <n="71"/>organic layer was then concentrated in vacuo to give 6.5 g (100percent) of the title compound as a brown solid.1 H NMR (400 MHz, DMSO-d6) δ ppm 2.99 (t, J=8.5 Hz, 2 H) 3.61 (t, J=8.4 Hz, 2 H) 3.78 (s, 3 H) 6.72 (s, 1 H) 7.28 (d, J=1 Hz, 1 H) 7.46 (d, J=2 Hz, 1 H); MS m/z 256/258 (1 :1 ratio) (M+1 )+ Rt 3.32 min. |
96% | at 25℃; for 16 h; | A mixture of methyl 5-bromo-1,N-(t-butoxycarbonyl)indoline-7-carboxylate (19.5 g, 54.7 mmol) in TFA (15 mL) was stirred at 25 °C for 16 hours. TLC (petroleum ether: ethyl acetate=10:1, Rf = 0.35) indicated that starting material was consumed completely and a major new spot with lower polarity was detected. The reaction was diluted with DCM (100 mL) and adjusted to pH=9 with sat. NaHCO3. The organic phase was separated and concentrated under reduced pressure to give compound methyl 5-bromoindoline-7-carboxylate (13.5 g, 96percent yield) as a brown solid. 1H NMR (400 MHz DMSO) = 7.45 (s, 1H), 7.27 (s, 1H), 6.72 (s, 1H), 3.77 (s, 3H), 3.61(m, 2H), 2.99 (m, 2H). ESI-MS (m/z): 260.0 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With manganese(IV) oxide In tetrahydrofuran at 20℃; Inert atmosphere | To a solution of 5-Bromo-2,3-dihydro-1 H-indole-7-carboxylic acid methyl ester (11.5 g, 45.1 mmol) in 10OmL THF was added MnO2 (39.2 g, 451 mmol). Then the mixture was stirred overnight at room temperature. The reaction was filtered and the filtrate was concentrated (10 g, 88percent). |
82% | With manganese(IV) oxide In dichloromethane at 25℃; for 48 h; | To a solution of methyl 5-bromoindoline-7-carboxylate (13.5 g, 52.7 mmol) in DCM (160 mL) was added MnO2 (45.8 g, 527 mmol). The mixture was stirred at 25 °C for 48 hours. TLC (petroleum ether : ethyl acetate=10:1, Rf = 0.3) indicated that startingmaterial was consumed completely and a major new spot with higher polarity was detected. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to afford of methyl 5-bromoindole-7-carboxylate (11 g, 82percent yield) as a brown solid. 1H NMR (400 MHz DMSO) = 11.38 (s, 1H), 8.06 (s, 1H), 8.79 (s, 1H), 7.47 (d, J=6 Hz, 1H), 6.56 (d, J=3.6 Hz, 1H), 3.93 (s, 3H). ESI-MS (m/z): 253.9 (M+H)+ |
80% | With manganese(IV) oxide In tetrahydrofuran at 20℃; for 112 h; | Methyl 5-bromo-2,3-dihydro-1 H-indole-7-carboxylate (6.5 g, 25 mmol) was dissolved in tetrahydrofuran (100 mL). Activated manganese dioxide (5 μm particle size, 22 g, 250 mmol) was added and the mixture stirred at room temperature for 16 hours. A further 22 g of activated manganese dioxide was added and the reaction stirred for 96 hours. The reaction was then filtered through celite and concentrated in vacuo to give 5.1 g (80percent) of the title compound as a beige solid.1 H NMR (400 MHz, DMSO-D6) δ ppm 3.94 (s, 3 H) 6.58 (d, J=3 Hz, 1 H) 7.48 (d, J=3 Hz1 1 H) 7.8 (d, J=2 Hz, 1 H) 8.07 (d, J=1.8 Hz, 1 H) 11.39 (bs, 1 H); MS m/z 252/254 (1 :1 ratio) (M-1) Rt 3.41 min. |
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