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CAS No. : | 141452-01-9 | MDL No. : | MFCD07371630 |
Formula : | C10H11NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VVAPQJBMJBCZMH-UHFFFAOYSA-N |
M.W : | 177.20 | Pubchem ID : | 21782110 |
Synonyms : |
|
Num. heavy atoms : | 13 |
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 : | 52.81 |
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) : | -5.9 cm/s |
Log Po/w (iLOGP) : | 2.04 |
Log Po/w (XLOGP3) : | 2.09 |
Log Po/w (WLOGP) : | 0.87 |
Log Po/w (MLOGP) : | 1.55 |
Log Po/w (SILICOS-IT) : | 2.0 |
Consensus Log Po/w : | 1.71 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.46 |
Solubility : | 0.608 mg/ml ; 0.00343 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.52 |
Solubility : | 0.529 mg/ml ; 0.00299 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.07 |
Solubility : | 0.149 mg/ml ; 0.000843 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.59 |
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 |
---|---|---|
99% | at 0 - 20℃; for 1.08333 h; | To a solution of lH-Indole-5-carboxylic acid methyl ester (1 g, 5.71 mmol) in 10 mL of acetic acid at 0 0C, was added sodium cyanoborohydride (1.08 g, 17.18 mmol) over 5 minutes. The mixture was stirred at room temperature for Ih. Water (3 mL) was added and all the solvents were removed under vacuum. The residue was dissolved in ethyl acetate (150 mL) and saturated NaHCCh (150 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3 x 75 mL). The combined extracts were washed with brine (150 mL), dried, filtered and evaporated. The residue was purified by flash chromatography (0-50percent ethyl acetate in hexane + 0.1percent triethylamine) to afford 0.99 g (99percent) of 19a. |
92% | at 0 - 20℃; for 2 h; | To a solution of 16 (0.30 g, 1.71 mmol) in AcOH (2 mL) was added sodium cyanoborohydride (0.16 g, 2.57 mmol) at 0° C., and allowed to stir at room temperature for 2 h. The reaction was quenched with water at 0° C., concentrated NaOH was added up to pH 10. The aqueous layer was extracted with CH2Cl2 (15 mL*3). The combined organic layer was dried over anhydrous MgSO4 and purified by chromatography over silica gel to afford 17 as a yellow solid (92percent yield; 1:2 EtOAc/n-hexane): 1H NMR (500 MHz, CDCl3) δ 3.06 (t, J=8.5 Hz, 2H), 3.65 (t, J=8.5 Hz, 2H), 3.84 (s, 3H), 6.54 (dd, J=8.6, 4.7 Hz, 1H), 7.75-7.76 (m, 2H). |
80% | Stage #1: With sodium cyanoborohydride In acetic acid at 0 - 20℃; for 1 h; Stage #2: With water In acetic acid |
Step 1: Methyl 2, 3-Dihydro-lH-indole-5-carboxylate (20);. [0192] To a cold solution of methyl indole-5-carboxylate (2 g, 11.4 mmol) in glacial acetic acid at 0°C (15 ml) sodium cyanoborohydride (1.075 g, 17.1 MMOL) was slowly added. The mixture was allowed to warm-up and stirred at room temperature for one more hour, cooled again to 0°C and quenched with H20. The pH of the resultant solution was adjusted to the value of 12 by adding aqueous NAOH, extracted with DCM, washed with brine and dried over MGS04. The dried extract was concentrated in vacuum and purified by flash chromatography (eluent 30percent EtOAc in hexane) to give the title compound 20 (1.62 g, 80percent) as a beige SOLID. 1H-NMR (DMSO) 8 : 2.94 (t, J = 8. 6 Hz, 2H); 3.51 (dt, J = 1.2, 8.6 Hz, 2H); 3.71 (s, 3H); 6.42 (d, J = 8.0 Hz, 2H); 7.54 (m, 2H). |
68% | With sodium cyanoborohydride In acetic acid at 20℃; for 1 h; Cooling with ice | Preparation of Compound 28,4 methyl indoline-5-carboxylate [0043] A mixture of methyl indole-5-carboxylate (0.500 g, 2.85 mmol) in AcOH (5 mL) was warmed to dissolve all solid. The solution was then cooled in an ice bath, and sodium cyanoborohydride (0.538 g, 8.56 mmol) was added portionwise over 10 min. Note that upon addition, the solution froze, thus was warmed a bit in order to achieve stirring, and occasionally cooled during the addition. After the addition was complete, the reaction mixture was allowed to warm to rt, and stirred for 1 hr. Water (1 .5 mL) was added, and the reaction mixture was concentrated to leave a viscous oil. EtOAc was added, washed with saturated NaHC03(aq) (2x). The aqueous phase was extracted with EtOAc (2x). The combined organic phases were washed with brine (1 x), dried (MgS04), filtered and concentrated. The crude material was purified by silica gel columnchromatography using 1 :1 PE to afford the title compound (344 mg, 68percent) as a white solid. 1H NMR (500 MHz, CDCI3) δ 7.77-7.74 (m, 2H), 6.55 (d, J = 8.6 Hz, 1 H), 4.1 1 (br s, 1 H), 3.84 (s, 3H), 3.65 (t, J = 8.5 Hz, 2H), 3.06 (t, J = 8.5 Hz, 2H). HRMS (ESI+): calcd for C10H12NO2 (M + H)+, 178.0863; found 178.0865. |
65% | Stage #1: for 1 h; |
Intermediate 5: 2,3-Dihydro-lH-indole-5-carboxylic acid methyl ester Methyl indole-5-carboxylate (1 g, 11.4 mmol) dissolved in glacial acetic acid (10 mL) was stirred at room temperature for 10 minutes. To this sodium cyanoborohydride (1.8 g, 28 mmol) was added slowly and the stirring continued for 1 hour. On completion of reaction, it was quenched by the addition of saturated sodium bicarbonate solution (150 mL) and extracted with ethyl acetate (2 x 100 mL). The organic layer was separated, dried over anhydrous Na2S04 and concentrated under reduced pressure to get the title product (0.65 g, Yield 65percent). NMR (DMSO-d6) 6(ppm): 3.23 (2H, t, -CH2), 3.61 (2H, t, -CH2), 4.0 (3H, s, -OCH3), 6.8 (1H, d, Ar-H), 7.6-7.65 (2H, m, Ar-H), 8.45 (1H, brs, -NH); MS m/z: 178.1 (M+l). |
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