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CAS No. : | 703-82-2 | MDL No. : | MFCD06657152 |
Formula : | C9H6ClNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CTNIXLBHXMSZKL-UHFFFAOYSA-N |
M.W : | 179.60 | Pubchem ID : | 12614669 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.7 |
TPSA : | 32.86 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) : | -5.88 cm/s |
Log Po/w (iLOGP) : | 1.54 |
Log Po/w (XLOGP3) : | 2.14 |
Log Po/w (WLOGP) : | 2.63 |
Log Po/w (MLOGP) : | 1.45 |
Log Po/w (SILICOS-IT) : | 3.29 |
Consensus Log Po/w : | 2.21 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.79 |
Solubility : | 0.291 mg/ml ; 0.00162 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.46 |
Solubility : | 0.62 mg/ml ; 0.00345 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.85 |
Solubility : | 0.0256 mg/ml ; 0.000143 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.22 |
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 |
---|---|---|
85% | Stage #1: at 0℃; for 1 h; Stage #2: at 20℃; for 5 h; Stage #3: With sodium hydroxide In N,N-dimethyl-formamide at 100℃; for 0.166667 h; |
General procedure: Oxalyl chloride (0.3 mL) was added in a drop-wise manner to cooled (ice-bath) DMF (3 mL) under stirring. The mixture was then stirred at 0 °C for 1 h. A solution of the substituted indole (4 mmol) in DMF (1.5 mL) was then added to the reaction mixture in a dropwise manner. The resulting mixture was stirred at room temperature for 5 h. A 2 N solution of sodium hydroxide (2 mL) was then added, and the mixture was heated at 100 °C for 10 min. The mixture was then cooled and extracted with ethyl acetate (3 X 50 mL). The organic layers were combined and washed with sequentially water and brine. The organics were dried (Na2SO4) and distilled to dryness to give the crude residue, which was purified by flash column chromatography using ethyl acetate/petroleum ether (3:1, v/v) as the eluent to give pure indole-3-carbaldehyde (4a-k). |
85% | Stage #1: at 60℃; for 1 h; Stage #2: With sulfuric acid In water at 50℃; for 1 h; |
Example 1: Step 1: 6-chloro-lH-indole-3-carbaldehvde [00331] A solution of 6-Chloro-lH-indole (1.0 g, 6.59 mmol) and phosphorus oxychloride (8.56 mmol) in dimethylformamide (12 mL) was heated at 60°C for lh. Water (5 mL) andconcentrated sulfuric acid (3.95 mmol) were added to the reaction mixture then heated at 50°C for 1 h. The mixture was concentrated and the residue was diluted with water (15 mL). The aqueous phase was extracted with ethyl acetate (3 x 25 mL). The organic extracts were combined and concentrated. Purification of the residue over silica gel, 0-75percent ethyl acetate in hexanes, afforded the title compound (1.01 g, 85percent) as a tan solid. LCMS [M+H] calculated: 179.6; observed: 179.9 |
85% | Stage #1: at 60℃; for 1 h; Stage #2: With sulfuric acid In water at 50℃; for 1 h; |
j00370j A solution of 6-chloro-1H-indole (1.0 g, 6.59 mmol) and POC13 (8.56 mmol) in DMF (12 mL) was heated at 60°C for lh. Water (5 mL) and concentrated sulfuric acid (3.95 mmol) were added and the mixture then heated at 50°C for 1 h. The mixture was concentrated and the residue was diluted with water (15 mL). The aqueous phase was extracted with EtOAc (3 x 25 mL). The organic extracts were combined and concentrated. Purification of the residue over silica gel, 0-75percent EtOAc in hexanes, afforded the title compound (1.01 g, 85percent) as a tan solid. LCMS [M+H]: 179.9 |
75% | at 0 - 20℃; for 3.5 h; | A solution of 6-chloroindole (30 mmol) in N,N-dimethylformamide (DMF) (5 mL) was added dropwise to a solution of phosphorus oxychloride (44 mmol) in DMF (32 mL) which had been stirred for 1.5 h at 0°C. The reaction mixture was warmed to room temperature and stirred for 2 h. The solution with the precipitate formed was poured on ice and basified with solid KOH and left overnight. The precipitate was filtered and washed with a mixture of 10percent ethyl acetate in petroleum benzene several times, then left to dry to give the aldehyde. 6-Chloro-1H-indole-3-carbaldehyde (3) Synthesized according to the general procedure of Vilsmeier–Haack reaction; light brick red solid; yield 4.04 g (75percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With water; iodine; oxygen; sodium carbonate In 1,4-dioxane at 100℃; for 36 h; Schlenk technique; Sealed tube | General procedure: Under air, a 20 mL of Schlenk tube equipped with a stir bar was charged with indole 1 (0.2 mmol, 1 equiv),TMEDA (75 µL, 0.5 mmol, 2.5 equiv), Na2CO3 (42.4 mg, 0.4mmol, 2.0 equiv), 1,4-dioxane (0.5 mL) and H2O (100 µL). Then I2 (101.5 mg, 0.4 mmol, 2.0 equiv) was added and the tube was sealed with a rubber plug and charged with O2. The reaction mixture was stirred at 100 °C for 36 h in oil bath. After cooling to room temperature, the resultant mixture was evaporated with EtOAc (20 mL) under reduced pressure and the residue was purified by flash column chromatography on a silica gel to give the products. |
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