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CAS No. : | 4382-54-1 | MDL No. : | MFCD00005614 |
Formula : | C10H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YEBJVSLNUMZXRJ-UHFFFAOYSA-N |
M.W : | 191.18 | Pubchem ID : | 20401 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 51.75 |
TPSA : | 62.32 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.85 cm/s |
Log Po/w (iLOGP) : | 1.41 |
Log Po/w (XLOGP3) : | 2.28 |
Log Po/w (WLOGP) : | 1.87 |
Log Po/w (MLOGP) : | 0.8 |
Log Po/w (SILICOS-IT) : | 1.87 |
Consensus Log Po/w : | 1.65 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.81 |
Solubility : | 0.299 mg/ml ; 0.00157 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.23 |
Solubility : | 0.114 mg/ml ; 0.000594 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.79 |
Solubility : | 0.312 mg/ml ; 0.00163 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.4 |
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 |
---|---|---|
80% | Stage #1: With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.166667 h; Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5 h; Stage #3: at -20℃; for 0.5 h; |
To a solution of 2-Bromo-5-methoxy-1H-indole (1.0 g,4.4 mmol, 1.0 equiv.) in dry THF (20 mL) at 0 C was added a 2 M solution of i-PrMgCl in THF(2.2 mL, 4.4 mmol, 1.0 equiv.) during 5 min. The clear solution was stirred at that temperature for anadditional 5 min, and a 2.5 M solution of n-BuLi in hexanes (3.5 mL, 8.8 mmol, 2.0 equiv.) was addeddropwise during 5 min, while maintaining the temperature below 20 C. The resulting mixture wasstirred at that temperature for 0.5 h, dry CO2 (0.20 g, 1.0 equiv.) was added to 20 C. The resultingmixture was warmed to 20 C in 0.5 h and quenched with water (6 mL). After stirring the mixturebelow 20 C for 10 min, the phases were separated and the water phase was extracted one additionaltime with ethyl acetate. The resulting suspension was allowed to reach room temperature and ®teredthrough a 0.5 1 cm pad of silica gel eluted with 10 mL of ethyl acetate. The ®ltrate was concentratedand the residue was puri®ed by ash chromatography on silica gel (eluent: petroleum ether/ethylacetate = 3:1) to afford product 3f as brown solid, 0.68 g (yield: 80percent), m.p.: 199–201 C. 1H-NMR(600 MHz, DMSO) 7.36 (d, J = 8.9 Hz, 1H), 7.06 (d, J = 23.6 Hz, 2H), 6.90 (d, J = 8.8 Hz, 1H), 3.73 (s, 3H).13C-NMR (151 MHz, DMSO) 163.25, 154.31, 133.07, 129.10, 127.65, 116.28, 113.83, 107.47, 102.44, 55.61. |
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