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CAS No. : | 214360-60-8 | MDL No. : | MFCD02093722 |
Formula : | C14H20BNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ANGKVUVZQVUVJO-UHFFFAOYSA-N |
M.W : | 261.12 | Pubchem ID : | 2734619 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 77.23 |
TPSA : | 47.56 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.42 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.08 |
Log Po/w (WLOGP) : | 1.75 |
Log Po/w (MLOGP) : | 1.13 |
Log Po/w (SILICOS-IT) : | 1.46 |
Consensus Log Po/w : | 1.28 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.81 |
Solubility : | 0.409 mg/ml ; 0.00157 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.71 |
Solubility : | 0.511 mg/ml ; 0.00196 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.39 |
Solubility : | 0.0107 mg/ml ; 0.000041 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.7 |
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 |
---|---|---|
93% | With tert.-butylnitrite; dibenzoyl peroxide In acetonitrile at 20℃; for 1 h; | Example 6 Synthesis of N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide B2pin2 (1.2 mmol, 305 mg), benzoyl peroxide (0.02 mmol, 5 mg), N-(4-aminophenyl)acetamide (1 mmol, 150 mg) and acetonitrile (3 mL) were added in a 25 mL tube-type reactor, followed by the addition of tert-butyl nitrite (1.5 mmol, 154 mg). The reaction was conducted at room temperature for 1 h. The solution was concentrated after the reaction and the resultant was purified by column chromatography (eluted by petroleum ether:ethyl acetate=20:1, V:V) to give N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide having the following structure: This compound is white solid and obtained in 93percent yield. Its NMR data are as follows: 1H NMR (400 MHz, CDCl3) δ 7.76 (d, 1H, J=8.4 Hz), 7.53 (d, 1H, J=8.3 Hz), 2.16(s, 3H), 1.33~1.24(m, 12H); 13C NMR (100 MHz, CDCl3) δ 168.5, 140.5, 135.6, 128.8, 119.9, 118.5, 83.6, 74.9, 24.9, 24.7, 24.5, 24.4. |
93% | With tert.-butylnitrite; dibenzoyl peroxide In acetonitrile at 20℃; for 1 h; | B2pin2 (1.2 mmol, 305 mg), benzoyl peroxide (0.02 mmol, 5 mg), N-(4-aminophenyl)acetamide (1 mmol, 150 mg) and acetonitrile (3 mL) were added in a 25 mL tube-type reactor, followed by the addition of tert-butyl nitrite (1.5 mmol, 154 mg). The reaction was conducted at room temperature for 1 h. The solution was concentrated after the reaction and the resultant was purified by column chromatography (eluted by petroleum ether : ethyl acetate = 20:1, V:V) to give N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide having the following structure: This compound is white solid and obtained in 93percent yield. Its NMR data are as follows: 1H NMR (400MHz, CDCl3) δ 7.76 (d, 1H, J=8.4Hz), 7.53 (d, 1H, J=8.3Hz), 2.16(s, 3H), 1.33~1.24(m, 12H); 13C NMR (100MHz, CDCl3) δ 168.5, 140.5, 135.6, 128.8, 119.9, 118.5, 83.6, 74.9, 24.9, 24.7, 24.5, 24.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; triethylamine In 1,4-dioxane at 20 - 100℃; Inert atmosphere | To a solution of compound 47 (250 mg, 1.45 mmol) in dioxane(6 mL) at room temperature was added bis(pinacolato)diboron(554 g, 2.18 mmol, 1.5 equiv.), and KOAc (427 mg, 4.35 mmol, 3equiv.). The reaction mixture was degassed under N2. Pd(dppf)Cl2(90 mg, 0.12 mmol, 0.1 equiv.) was added to the mixture anddegassed under N2. The reaction mixture was heated to 100 C andstirred overnight under nitrogen. The reaction mixture was monitoredusing TLC until completion, filtered through Celite andwashed with EA. The reaction solvent was evaporated underreduced pressure to give a residue, which was purified via silica gelcolumn chromatography (elution system - EA/Hexane 1: 1) togive compound 48 as a white solid (870 mg, 71percent).Rf 0.43 (EA/Hexane 1: 1); 1H NMR (400 MHz, CDCl3) d 7.76(d, J 8.3 Hz, 2H), 7.51 (d, J 7.9 Hz, 2H), 7.19 (s, 1H), 2.18 (s, 3H),1.33 (s, 12H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 100℃; for 4 h; Inert atmosphere | To a stirred solution of CI (300 mg, 1.14 mmol) in DMSO (15 mL) under inert atmosphere were added bis(pinacalato)diboron (321 mg, 1.26 mmol) and fused potassium acetate (338 mg, 3.44 mmol) at RT. The reaction was purged with argon for 30 min. Then Pd(dppf)2Cl2 (84 mg, 0.11 mmol) was added to the reaction mixture and the reaction was heated to 100 °C and stirred for 4 h. After complete consumption of the starting material, the reaction mass was cooled to RT, was diluted with water (20 mL), and was extracted with EtOAc (2x20 mL). The combined organic extracts were washed with water (20 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The crude was purified by silica gel column chromatography (5percent MeOH/CH2Cl2) to afford CJ (150 mg, 50percent) as a brown solid. *H NMR (500 MHz, CDC13): δ 7.76 (d, J = 8.0 Hz, 2H), 7.51 (d, J = 8.0 Hz, 2H), 7.17 (br s, 1H), 2.18 (s, 3H), 1.33 (s, 12H). MS (ESI): m/z 262 [M+l]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81 %Chromat. | With triethylamine In 1,4-dioxane at 80℃; for 5 h; | [00168] To 25 mg PdCl2(dppf).CH2Cl2 in a reaction tube under nitrogen were added 4 ml dioxane, 0.43 ml (3 mmol) triethylamine, 0.47 ml (3.2 mmol) pinacolborane and 262 mg (1.0 mmol) p-iodoacetanilide. The p-iodoacetanilide did not react with the pinacolborane to liberate hydrogen. The reaction solution was warmed to 80 C. with stirring in an oil bath. After 1 h the solution had darkened and an aliquot (0.3 ml) was removed from the reaction solution, extracted into diethyl ether, washed several times with water and analysed by gc (fid detector, SGE HT5 capillary column). There was only one strong peak (of area 74percent of total peak areas, uncorrected for response factors) in the gc and that was shown by gc/ms to be due to the desired arylboronic acid pinacol ester. On heating the reaction mixture for a further 4 h at 80 C., the apparent yield of the required boronic acid ester increased to 81percent while that of the acetanilide and phenylboronic acid pinacol ester peak areas were 14percent and 3.4percent respectively. |
90 %Chromat. | Stage #1: With triethylamine In 1,4-dioxane at 80℃; for 7.5 h; Stage #2: at 80℃; for 5 h; |
[00240] The catalyst amount in this reaction was reduced to approx. {fraction (1/35)} that used in the small scale reactions. The molar ratio of catalyst:iodide:pinacolborane:NEt3 is 1:1150:1500:2933. The amount of pinacolborane was 1.25 equivalents compared to the iodide. The pinacolborane was made from BH3?e2 by reaction with pinacol in dioxane. 50 ml of BH3?e2 were dissolved in 100 ml of dioxane in a 1 L Schlenk flask. To this was added dropwise 63.0 g of pinacol in 140 ml dioxane. After the addition was complete the solution was stirred at room temp. and then at 60 C. to ensure complete reaction of the BH3?e2. The solution contained a little white precipitate. [00241] The catalyst was activated prior to use by heating 1500 mg of PdCl2[dppf].CH2Cl2 with 30 ml of triethylamine in 370 ml dioxane at 80 C. from for 7.5 h. 67 ml of this dark brown solution was used in the reaction. [C00065] [00242] To the pinacolborane solution was added 120 ml (863 mmol) dry triethylamine, 92 g (352.5 mmol) p-iodoacetanilide and then 67 ml of the catalyst solution. The reaction solution was placed in the oil bath at 80 C. The solution became clear and pale brown in colour and after about 1 to 2 h, a precipitate of the amine.HI salt separated. After 5 h the reaction was over 90percent complete. Heating was continued for several more hours after which no starting material was observed, by gc, to be in the reaction solution. The reaction product in a number of such reactions was always over 90percent by gc, the only side product observed was acetanilide. No phenylboronic acid pinacol ester were seen in the gc unless very strong solutions were employed. [00243] The crude product was isolated by removing the amine salt from the solution at room temp. The excess pinacolborane was destroyed with dry methanol. After reducing the volume of the reaction solution, the product was precipitated with petroleum ether. The dark coloured impurity in the product was removed by passing a solution of the product in toluene through a short column of Merck type 9385.1000 silica gel 60. The product was obtained as a white solid, mp>162 C. from toluene. [00244] The presence of borane methyl sulfide complex in these reactions does not stop the reaction from progressing. It can retard rate of the reaction somewhat but indications are that it can retard, especially with certain substrate, the dehalogenation reaction to a greater extent than the boronation reaction and so lead to an increase in product yield. |
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