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CAS No. : | 1204-32-6 | MDL No. : | MFCD06245515 |
Formula : | C11H11NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NMILWYUYIFMKTE-UHFFFAOYSA-N |
M.W : | 189.21 | Pubchem ID : | 639843 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.18 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 54.48 |
TPSA : | 31.23 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) : | -6.14 cm/s |
Log Po/w (iLOGP) : | 2.39 |
Log Po/w (XLOGP3) : | 1.85 |
Log Po/w (WLOGP) : | 1.96 |
Log Po/w (MLOGP) : | 1.67 |
Log Po/w (SILICOS-IT) : | 1.79 |
Consensus Log Po/w : | 1.93 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.52 |
Solubility : | 0.568 mg/ml ; 0.003 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.13 |
Solubility : | 1.41 mg/ml ; 0.00747 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.92 |
Solubility : | 0.225 mg/ml ; 0.00119 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.47 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-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 |
---|---|---|
99% | With methanol; sodium hydroxide; water In tetrahydrofuran at 20℃; for 36 h; | Step 2: 1-Methyl-lH-indole-6-carboxylic acid (167) [0334] Methyl 1-METHYL-LH-INDOLE-6-CARBOXYLATE 166 (1.24 MMOL) was stirred with sodium hydroxide (0.59g, 14.88 MMOL) in a 2: 2: 1 mixture of methanol/THF/water (7.5 mL) for 36 hrs at rt to form a precipitate which was collected by filtration and LYOPHILIZED overnight to give the title compound 167 (0.54g, 99percent yield). MS: 175.06 (CALC), 176.1 (OBS). |
86% | Stage #1: With lithium hydroxide In tetrahydrofuran; methanol; water; acetonitrile at 20℃; Stage #2: With hydrogenchloride In water |
To N-methylindole-6-carboxylic acid methyl ester in 3 mL 1 :1:1 :1 acetonitrile/THF/water/MeOH was added LiOH and allowed to stir at room temperature over the weekend. The reaction mixture was concentrated under reduced pressure before adding EtOAc and water. The organic phase was separated and the water acidified with 1N HCI and extracted into EtOAc (3x50 mL), washed with water, saturated aqueous NaCI1 dried over MgSO4, filtered, and concentrated under reduced pressure. The material was dried under reduced pressure to afford the title product (0.16 g, 86percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5 h; Stage #2: at 20℃; for 20 h; |
To a stirred solution of methyl 1 H-indole-6-carboxylate (0.76g, 4.34mmol) in DMF (10ml) at room temperature was added sodium hydride (0.35g, 8.75mmol). The resultant suspension was stirred for 30min at room temperature followed by the addition of methyl iodide (0.54ml, 8.67mmol). The reaction mixture was stirred for 2Oh at room temperature and was then quenched by the addition of water (20ml) and ethyl acetate (20ml). The aqueous layer was extracted with ethyl acetate (3 x 30ml) and the combined extracts were dried with a phase separating column. The solvent was then removed in vacuo to give the desired product as an off-white solid (0.85g, 100percent). LC-MS (Acidic) (MH+=I 90). The product was used without further purification |
100% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1 h; Stage #2: at 20℃; for 15 h; |
Method D; 1 -methyl-1 /-/-indole-6-carboxylic acid methyl ester (Intermediate compound); A mixture of methyl-indole-6-caroxylate (3.0 g, 16.6 mmol), sodium hydride (1.0 g, 24.9 mmol), DMF (20 ml) was stirred for 1 h at room-temperature followed by addition of iodomethane (4.7 g, 33.2 mmol) and stirring at room- temperature for 15 h. The mixture was extracted with chloroform and evaporated. The product was isolated by evaporation. Yield 3.2 g (100percent). |
1.16 g | With potassium hydroxide In dimethyl sulfoxide at 20℃; for 1 h; | Method 3 Synthesis of methyl 1-methylindole-6-carboxylate (Intermediate 4) To a solution of R-3 (1 g, 5.7 mmol) in DMSO (10 mL) is added KOH (800 mg, 14.3 mmol) and iodomethane (0.534 mL, 8.6 mmol). After stirring at room temperature for 1 h the reaction mixture is diluted with water (50 mL) and the resultant suspension filtered and washed with more water. The solid is dried in vacuo to give the title intermediate I-4 (1.16 g) m/z 190.0 [M+H]. |
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