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CAS No. : | 877-03-2 | MDL No. : | MFCD00152016 |
Formula : | C9H6BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PEENKJZANBYXNB-UHFFFAOYSA-N |
M.W : | 224.05 | Pubchem ID : | 70137 |
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 : | 51.39 |
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) : | -6.1 cm/s |
Log Po/w (iLOGP) : | 1.59 |
Log Po/w (XLOGP3) : | 2.2 |
Log Po/w (WLOGP) : | 2.74 |
Log Po/w (MLOGP) : | 1.6 |
Log Po/w (SILICOS-IT) : | 3.33 |
Consensus Log Po/w : | 2.29 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.1 |
Solubility : | 0.176 mg/ml ; 0.000787 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.52 |
Solubility : | 0.67 mg/ml ; 0.00299 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.09 |
Solubility : | 0.0182 mg/ml ; 0.0000811 mol/l |
Class : | Moderately 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-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
65% | With sodium hydroxide In acetic acid | EXAMPLE 153 5-(2-Dimethylaminomethyl-cyclopropylmethyl)-1H-indole-3-carbonitrile Commercially available 5-bromoindole-3-carboxaldehyde (11.3 g, 50.4 mmol), ammonium hydrogen phosphate (47.0 g, 353 mmol), 1-nitropropane (4.49 g, 50.4 mmol), and glacial acetic acid (100 ml) were heated at a gentle reflux for 18 h. The resulting mixture was concentrated in vacuo and the residue mixed with 5 N sodium hydroxide (500 ml) and ice chips. The precipitate was collected by filtration and rinsed several times with water. The filtrate was concentrated in vacuo to afford 5-bromo-3-cyanoindole (7.23 g, 65percent) as a dark solid. 1H-NMR (400 MHz, CDCl3) δ10.0 (1 H, s), 8.68 (1 H, br s), 8.51 (1 H, s), 7.85 (1 H, s), 7.43 (1 H, dd, J=8.6, 1.9 Hz), 7.32 (1 H, d, J=8.6 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With acetic acid In water; 1-Nitropropane | 5-Bromo-7-methyl-1H-indole-3-carbonitrile A mixture of 5-bromo-indole-3-carboxaldehyde (0.7 g, 2.94 mmol), diammonium hydrogen phosphate (2.05 g, 15.5 mmol) in 1-nitropropane (9 mL) and acetic acid (3 mL) were heated at reflux for 16 h. After cooling to room temperature, the solvents were removed under reduced pressure and water added to the dark residue. After a short while, 5-bromo-1H-indole-3-carbonitrile precipitated rapidly, was filtered, washed severally with water and dried for several hours to afford 0.6 g (87percent) of the desired nitrile. LC/MS: tR=1.71 min, 235.01 (MH)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With potassium permanganate; water In acetone at 20℃; for 6.5 h; | General procedure: 6 g of substituted indole-3-aldehydes (10a–b) was dissolved in 600 mL of acetone.To this KMnO4 (9 g, 56 mmol) soluble in 180 mL water was added slowly for 30 min and the reaction mixture was allowed for stirring for 6 h at room temperature. After it was quenched by 6 mL of 30percent H2O2, filtered and concentrated on rotavapor. Now it was solidified by conc.HCl, filtered, dried and recrystallized from methanol solvent which then afforded 5-substituted indole-3-carboxylic acids 11a–b. 5-Bromo-1H-indole-3-carboxylic acid (11b) (Yoo et al.2012) yellow color solid. yield: 65percent. m.p: 230–232 °C; IR (KBr): 3349, 2914, 2574, 1643 cm−1; 1H NMR (400 MHz, DMSO-d6): δ 7.30 (1H, m, Ar–H), 7.435 (1H, d, J = 8.8 Hz, Ar–H), 8.05 (1H, d, J = 2.8 Hz, Ar–H), 8.12 (1H, d, J = 2 Hz, Ar–H), 12.01 (1H, bs, -NH), 12.13 (1H, s, -OH) ppm; 13C NMR (400 MHz, DMSO-d6): δ 107.06, 113.79, 114.28, 122.68, 124.70, 127.79, 133.45, 135.16, 165.45 ppm; HRMS calculated for C9H6NO2BrNa: 261.94741; found: 261.94711. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 70℃; for 2 h; | (d) 5,5'-Dibromo-3,3'-dimethyl-2,2'-diindolylmethane (42). To a solution of aldehyde 40 (1.51 g, 6.74 mmol) in THF (35 mL) was added LiAlH4 (0.51 g, 13.48 mmol) at 0° C. and then heated to 65-70° C. for 2 h under argon. The suspension was cooled to 0° C. and quenched with water, and white precipitate was removed by filtration. The filtrate was dried (MgSO4) and concentrated to afford 5-bromo-3-methylindole (41) as a solid (1.16 g, 82percent). To a mixture of 39 (1.2 g, 5.0 mmol) and 41 (1.0 g, 4.76 mmol) in CH2Cl2 (25 mL) was added (CF3SO3)3Sc (0.23 g, 0.47 mmol) and stirred overnight under argon. The solvent was evaporated to give a crude product. Flash chromatography (10percent EtOAc/hexane) yielded 42 as a white solid (1.91 g, 93percent): 1H NMR (300 MHz, CDCl3) δ 2.29 (s, 6, CH3), 4.21 (s, 2, CH2), 7.08 (d, J=8.5 Hz, 2, ArH), 7.22 (dd, J=1.8, 8.5 Hz, 2, ArH), 7.66 (d, J=1.8 Hz, 2, ArH), 7.67 (br.s, 2, NH). |
73% | With lithium aluminium tetrahydride In tetrahydrofuran for 2 h; Reflux | Ste 2. 5-Bromo-3-methyl-7H-indoleTo a solution of 5-bromo-7H-indole-3-carbaldehyde (5.0 g, 22.3 mmol) in THF (80 mL) was added L1AIH4 (1.70 g, 44.6 mmol). The resulting solution was stirred for 2h under reflux, then poured into IN NaOH solution (150 mL), extracted with ethyl acetate (3 x 100 mL), dried over anhydrous sodium sulfate, and then concentrated under vacuum to give a residue, which was purified via silica gel chromatography (3percent ethyl acetate in petroleum ether) to afford 5-bromo-3-methyl-7H-indole as a white solid (3.4 g, 73percent).'H-NMR (300 MHz, CDCI3): 5:7.91 (s, 1H), 7.72 - 7.73 (t, /= 0.9 Hz, 1H), 7.21 - 7.30 (m, 2H), 6.99 (d, /= 0.9 Hz, 1H), 2.31 (s, 3H) |
44.7% | With lithium aluminium tetrahydride In tetrahydrofuran for 8.5 h; Reflux | A solution of 5-bromo-1H-indole-3-carbaldehyde (13.12 g, 58.6 mmol) in THF (100 mL) was added to a refluxing mixture of LiA1H4 (4.89 g, 129 mmol) in THF (100 mL) (reflux condenser fitted to a two neck flask) over 30 mm. The reaction mixture was refluxed for 8 hours, cooled to room temperature and treated with diethyl ether (50 mL). The reaction mixture was acidified to pH 3 with iN HC1, while cooling in an ice bath. The reaction mixture was diluted with ethyl acetate (125 mL), poured into a separatory funnel and washed with water (2X 50 mL) and saturated aqueous sodium chloridesolution (50 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give crude product. The crude product was dissolved in a small amount of DCM and charged to an ISCO silica gel (80 g) column, which was eluted over 15 minutes using a gradient of 0-50percent ethyl acetate/heptane. The combined fractions were concentrated to give 5-bromo-3-methyl-1H-indole (5.5 g, 44.7percent yield). LCretention time 1.0 mm [Method Al]. MS (E) m/z: 210/212 (M-H). |
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