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CAS No. : | 261732-38-1 | MDL No. : | MFCD08059280 |
Formula : | C13H16BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UOCVSZYBRMGQOL-UHFFFAOYSA-N |
M.W : | 298.18 | Pubchem ID : | 21865438 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.46 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 75.08 |
TPSA : | 29.54 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.71 cm/s |
Log Po/w (iLOGP) : | 3.33 |
Log Po/w (XLOGP3) : | 3.39 |
Log Po/w (WLOGP) : | 3.37 |
Log Po/w (MLOGP) : | 3.19 |
Log Po/w (SILICOS-IT) : | 2.85 |
Consensus Log Po/w : | 3.23 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.89 |
Solubility : | 0.0386 mg/ml ; 0.00013 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.69 |
Solubility : | 0.061 mg/ml ; 0.000204 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.03 |
Solubility : | 0.0281 mg/ml ; 0.0000942 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.41 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H317-H319 | Packing Group: | |
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 |
---|---|---|
95% | at 20℃; for 18 h; | To a solution of 5-bromo-2,3-dihydro-1H-indole (2.11 g, 10.7 mmol) in 40 mL of THF was added Boc2O (2.56 g, 11.7 mmol). The reaction mixture was stirred at room temperature for 18 hours, and then concentrated under reduced pressure. Purification of the residue via flash chromatography (8percent EtOAc in hexane) afforded 5-bromo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (2.59 g, 95percent) as a white solid; MS (M+H)=298. |
89% | With sodium hydroxide In 1,4-dioxane; water | Part 1. To a solution of 5-bromoindoline (1.0 g, 5 mmol) in 10 ml of dioxane was added 5 mL of a 1N NaOH solution and 5 mL of water. This mixture was cooled with an ice bath, and di-tert-butyl dicarbonate (1.2 g, 5.5 mmol) was added in one portion. The reaction was allowed to warm to room temperature, stirred for 4 hours, and then concentrated. The residue was extracted with ethyl acetate (2*25 mL), and the combined organic phases were washed with water (2*25 mL), saturated aqueous NaCl (2*25 ml), then dried over MgSO4. Filtration and concentration in vacuo gave N-Boc-5-bromoindoline (1.33 g, 89percent) as a light brown powder after drying. 1H NMR (CDCl3) δ: 1.541 (s, 9H); 3.03-3.08 (t, 2H); 3.92-3.96 (t, 2H); 7.23-7.27 (m, 3H). |
80% | With potassium carbonate In tetrahydrofuran; water at 20℃; for 2 h; | Step 1: tert-butyl 5-bromoindoline-l-carboxylateTo a solution of 5-bromoindoline (280 mg, 1.41 mmol) in THF (15 mL) and H20 (5 mL) was added k2C03 (293 mg, 2.12 mmol), followed by di-tert-butyl dicarbonate (617 mg, 2.82 mmol) and the resulting mixture was stirred at room temperature for 2 hours. The mixture was diluted with water and extracted with EtOAc. The combined extract was washed with brine, dried and concentrated to afford desired product (338 mg, 80percent). 1H NMR (OMSO-d6): δ 7.59 (1H, br), 7.38 (1H, s), 7.30-7.32 (2H, m), 3.90 (2H, t, / = 8.8 Hz), 3.07 (2H, t, / = 8.8 Hz), 1.50 (9H, s). |
73% | With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16 h; | To a solution of 5-bromoindoline (3.3 g, 16.7 mmol) in DCM (33 mL) at room temperaturewas added 4-dimethylaminopyridine (0.21 g, 1.7 mmol), di-iso-propylethyl amine (4.3 g,33.4 mmol) and di-tert-butyldicarbonate (5.8 g, 26.7 mmol). The resulting mixture was stirred at room temperature for 16 h and then concentrated in vacuo. The crude residue was purified by silica gel chromatography (petroleum ether / EtOAc = 9: 1) to give the title compound (3.63 g, 73percent) as a white solid. |
55% | at 20℃; | A solution of 5-bromo-2,3-dihydro-1H-indole (4.97 g, 25.1 mmol), di-tert-butyl dicarbonate (6.0 g, 27.5 mmol) and 4-dimethylaminopyridine (catalytic) in dichloromethane (70 mL) was stirred at room temperature until the starting material was consumed. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography on silica gel, eluted with ethyl acetate/hexane to give the product, 4.1 g (55percent). 1H NMR (CDCI3) : δ 1.55 (s, 9 H), 3.06 (t, 2 H), 3.97 (t, 2 H), 7.23-7.27 (m, 2 H) and 7.72 (br m, 1 H). |
38% | With dmap In acetonitrile at 20℃; for 16 h; | 5-Bromoindoline (3.96 g, 20 mmol), di-t-butylcarbonate (4.37 g, 20 mmol), 4-dimethylaminopyridine (2.69 g, 22 mmol) and CH3CN (50 mL) were mixed and stirred at room temperature for 16 h. The reaction mixture was diluted with EtOAc (300 mL) and the organic solution was washed successively with water (50 mL), a 1 N HCl solution (50 mL), a saturated NaHCO3 solution (2.x.50 mL) and brine (25 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to afford a solid. Trituration with hexane and drying in vacuo provided a white solid (2.26 g, 38percent yield): 1H NMR (DMSO-d6, 300 MHz): 7.36 (s, 1H), 7.29 (d, 2H, J=7), 3.86 (t, 2H, J=7), 3.04 (t, 2H, J=7), 1.48 (s, 9H). |
Ca. 28.5 g | With dmap In acetonitrile at 20℃; for 3 h; | 1,1-Dimethylethyl 5-bromo-2,3-dihvdro-1 H-indole-1-carboxylate To a stirred solution of 5-bromo-2,3-dihydro-1 H-indole (30 g, 151 mmol) and DMAP (0.4 g, 3.27 mmol, 0.02 equiv) in 150 mL of MeCN at room temperature was added Boc20 (43 g, 197 mmol, 1.3 equiv) in one portion. The mixture was stirred at room temperature. After 10 min, the mixture gradually became a suspension. After 3 hours, the suspension was filtered. The cake was washed with cold MeCN (60 mL), and dried under house vacuum for 5 hours to give 1 ,1-Dimethylethyl 5-bromo-2,3-dihydro-1 H-indole-1- carboxylate (ca. 28.5 g prior to drying). LCMS (ES) m/z = 244, 242 as prominent fragments. 1 H NMR (400 MHz, DMSO-d6) δ ppm 1.50 (s, 9 H), 3.06 (t, J=8.7 Hz, 2 H),3.91 (t, J=8.7 Hz, 2 H), 7.31 (dd, J=8.5, 1.9 Hz, 1 H), 7.38 (s, 1 H), 7.51 - 7.71 (br s, 0.6 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | Stage #1: With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 2.08333 h; Stage #2: With acetic acid In tetrahydrofuran; pentane at -78 - 20℃; for 2 h; |
5-Bromo-1-t-butyloxycarbonylindoline (2.0 g, 6.7 mmol) and DMF (0.53 mL, 6.7 mmol), were dissolved in THF (30 mL) and the resulting solution was cooled to -78° C. with stirring under a nitrogen atmosphere. A solution of t-butyllithium in pentane (1.7 M, 10.3 mL, 17.5 mmol) was added dropwise over 5 min. The reaction mixture was stirred for 2 h; then HOAc (3 mL) was added. The cloudy mixture was warmed to ambient temperature over 30 min and diluted with EtOAc (100 mL). Successive washings with a saturated Na2CO3 solution (2.x.10 mL) and then brine (10 mL) were performed. Drying over Na2SO4, filtration and removal of solvent in vacuo gave an oil. Column chromatography (EtOAc:hexane: 1:9, then 1:1) and removal of solvent in vacuo provided two products, both were white solids: (1) 1-t-butyloxycarbonylindoline (270 mg, 18percent yield): 1H NMR (CDCl3, 300 MHz): 7.18-7.10 (m, 2H), 6.92 (t, 1H, J=7), 3.97 (t, 2H, J=7), 3.08 (t, 3H, J=7), 1.57 (s, 9H); MS (APCI+): 220 (C13H18NO2, M++H) and (2) the title product (650 mg, 39percent yield): 1H NMR (CDCl3, 300 MHz): 9.86 (s, 1H), 7.9 (br s, 1H), 7.70-7.65 (m, 2H), 4.06 (t, 2H, J=7), 3.15 (t, 2H, J=7), 1.58 (s, 9H); MS (ES+): 248 (C14H18NO3, M++H). |
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