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CAS No. : | 191171-55-8 | MDL No. : | MFCD02179448 |
Formula : | C12H18BNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZCJRWQDZPIIYLM-UHFFFAOYSA-N |
M.W : | 219.09 | Pubchem ID : | 2734652 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 67.32 |
TPSA : | 44.48 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 : | Yes |
Log Kp (skin permeation) : | -6.05 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.23 |
Log Po/w (WLOGP) : | 1.58 |
Log Po/w (MLOGP) : | 1.13 |
Log Po/w (SILICOS-IT) : | 1.12 |
Consensus Log Po/w : | 1.21 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.81 |
Solubility : | 0.336 mg/ml ; 0.00153 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.8 |
Solubility : | 0.348 mg/ml ; 0.00159 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.65 |
Solubility : | 0.0496 mg/ml ; 0.000226 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.79 |
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 |
---|---|---|
98% | In dichloromethane at 20℃; for 12h; | N-(4-Methoxybenzyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine (B). A pinacol (47.4 g,401.1 mmol) solution in 150 mL dichloromethane mixedwith (2-aminophenyl)boronic acid (50 g, 364.8 mmol) was stirred at room temperature for 12 h. Upon vacuumdistillation of the solvent the mixture 3 (white solid,78.3 g, yield 98%) was obtained, and it was used in thenext reaction without purification. A mixture of compound3 (10 g, 45.6 mmol) with 4-methoxy benzaldehyde (7.46 g,54.8 mmol) and AcOH (3.29 g, 54.8 mmol) was dissolvedin dichloromethane (80 mL) and stirred at 0°C for10 min, then NaBH(OAc)3 (16.45 g, 77.6 mmol) was addedslowly to it. The mixture was stirred at room temperaturefor 4 h then concentrated under reduced pressure. The pHof the mixture was adjusted to 9, and suction filtrationwas performed under reduced pressure. Compound Bwas obtained by washing the crude mixture with hexane.Yield 74.3%, mp 80.01-82.04°C. IR spectrum, ν, cm-1:3404 (NH), 1510 (C=C), 3036 (C6H5-H), 1242 (COC).1H NMR spectrum, δ, ppm: 7.71-7.69 d (1H, C6H4),7.35-7.33 d (1H, C6H4), 7.31 t (1H, C6H4), 6.94-6.92 d(2H, C6H4), 6.68 t (3H, C6H4), 6.57 s (1H, NH), 4.38 s(2H, CH2), 3.86 s (3H, CH3), 1.38 s (12H, CH3). 13CNMR spectrum, δC, ppm: 158.59, 137.07, 133.12, 128.19113.90, 83.55, 55.30, 47.07, 24.91. M 340.26. |
76% | In tetrahydrofuran | |
76% | In tetrahydrofuran stirred under N2 overnight; evapn., chromy. (SiO2, EtOAc/toluene); |
With magnesium(II) sulfate In dichloromethane at 20℃; Glovebox; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65 mg | With barium dihydroxide In 1,4-dioxane at 100℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 75 - 100℃; for 8.08333h;Inert atmosphere; | General procedure: A solution of 2 M Na2CO3 (10 mL) was added under nitrogen to a 2-bromoaniline (10 mmol) in 60 mL dioxane. After 5 min stirring at 75 C, Pd[P(C6H5)3]4 was added followed by (10 mmol) of a 2-cyanophenylboronic acid pinacol ester. The reaction was stirred 8 h at 100 C. After cooling to rt the mixture was vacuum concentrated to half of its initial volume and extracted with CH2Cl2 (30 mL) and water (30 mL). The aqueous phase was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The solid crystallized upon concentration. |
32% | With palladium diacetate; amantadine hydrochloride; caesium carbonate; In 1,4-dioxane; for 17h;Inert atmosphere; Reflux; | Step 1: Synthesis of 9-fluoro-6-phenanthridinamine To a solution of <strong>[60702-69-4]2-chloro-4-fluorobenzonitrile</strong> (1.0 g, 6.42 mmol), 2-aminophenylboronic acid pinacol ester (1.6 g, 7.1 mmol), palladium(III) acetate (0.07 g, 0.32 mmol), amantadine hydrochloride (0.24 g, 1.3 mmol) and cesium carbonate (4.6 g, 14.1 mmol) were added to dioxane previously deaerated with nitrogen and heated to reflux for 17 hours. After cooling, both distilled water and methylene chloride (50 mL) were added to the reaction mixture. The solvent layer was separated and concentrated to give a crude oil that was purified by column chromatography by first using 1:1 ethyl acetate and hexanes ratio followed by 4:1 ethyl acetate/hexanes as the eluants. The pure product was collected to give 9-fluoro-6-phenanthridinamine (42 g, 32% Yield) whose NMR spectrum is consistent with the proposed structure. |
32% | With palladium diacetate; amantadine hydrochloride; caesium carbonate; In 1,4-dioxane; for 17h;Inert atmosphere; Reflux; | Step 1: synthesis of 9-fluoro-6-phenanthridine amine <strong>[60702-69-4]2-chloro-4-fluorobenzonitrile</strong> (1.0 g, 6.42 mmol), 2-amino-phenylboronic acid pinacol ester (1.6 g, 7.1 mmol), palladium(II) acetate (0.07 g, 0.32 mmol), amantadine hydrochloride (0.24 g, 1.3 mmol) was added to cesium carbonate and dioxane was degassed with nitrogen in advance to a solution of (4.6 g, 14.1mmol) and heated to reflux for 17 hours. After cooling, distilled water was added to both, and methylene chloride (50 ) to the reaction mixture. Separating the solvent layer, and obtain a crude oils and concentrated, this 1 as eluent: purified by column chromatography using 1 ethyl acetate / hexane: 1 and then 4 in the ratio of ethyl acetate and hexane. Collecting the pure product were obtained 9-fluoro-6-phenanthridin-amine (42 g, 32% yield), and its NMR spectrum was consistent with the proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81 % Chromat. | With amantadine hydrochloride; caesium carbonate In 1,4-dioxane at 100℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 95℃; for 18h; | Step 2: LE29 (The following reaction is carried out in an N2 atmosphere.) Dissolve Tetrakis-(triphenylphosphine)-palladium(0) (510mg, 0.45 tnmol) and ester (46) (1.97g, 8.91mmol) in DME (16mL), degas the reaction mixture carefully (5 times) and flush with N2. Add 2-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenylamine (2.15g, 9.80mmol) and a 1 M aqueous NaHCO3 solution (27.OmL, 27.0mmol), degas the reaction mixture again carefully (5 times) and flush with N2. Stir the mixture for 18h at 95C. Partition the EPO <DP n="40"/>reaction solution between EtOAc and water and extract the separated aqueous layer with EtOAc (3 times). Wash combined organic layer with brine and dry it with Na2SO4. Purify the crude product by flash chromatography (silica gel, CyH/EtOAc 5+1] to obtain 5-(2- Amino-phenyl)-thiophene-2-carboxylic acid methyl ester (47) as a yellow solid (1.4 Ig, 67%). 1H NMR (400 MHz, CDCl3): 3.88 (s, 3 H); 4.00 (s, 2 H); 6.73-6.82 (m, 2 H); 7.13- 7.21 (m, 2 H); 7.26 (dd, 1 H, J1 = 7.6 Hz, J2 = 1.0 Hz); 7.78 (d, 1 H, J= 3.8 Hz). |
67% | With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 95℃; for 18h; | Step 2: LE29 (The following reaction is carried out in an N2 atmosphere.) Dissolve Tetrakis-(triphenylphosphine)-palladium(0) (510 mg, 0.45 mmol) and ester (46) (1.97 g, 8.91 mmol) in DME (16 mL), degas the reaction mixture carefully (5 times) and flush with N2. Add 2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (2.15 g, 9.80 mmol) and a 1 M aqueous NaHCO3 solution (27.0 mL, 27.0 mmol), degas the reaction mixture again carefully (5 times) and flush with N2. Stir the mixture for 18 h at 95 C. Partition the reaction solution between EtOAc and water and extract the separated aqueous layer with EtOAc (3 times). Wash combined organic layer with brine and dry it with Na2SO4. Purify the crude product by flash chromatography (silica gel, CyH/EtOAc 5+1] to obtain 5-(2-Amino-phenyl)-thiophene-2-carboxylic acid methyl ester (47) as a yellow solid (1.41 g, 67%). 1H NMR (400 MHz, CDCl3): 3.88 (s, 3H); 4.00 (s, 2H); 6.73-6.82 (m, 2H); 7.13-7.21 (m, 2H); 7.26 (dd, 1H, J1=7.6 Hz, J2=1.0 Hz); 7.78 (d, 1H, J=3.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With water; sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; for 16h; | Example (III-1) A solution of 0.67 g (3 mmol) 2- (4, 4,5, 5-tetramethyl-1, 3,2-dioxaborolan-2-yl) aniline, 0. 80 g (3 mmol) of 2-bromo-3-chloro-5- (trifluoromethyl) pyridine and 0.05 G (0.68 mmol) of L, l'-bis (diphenylphosphi- no) ferrocenpalladium (I chloride in 15 ml dimethyl sulphoxide and 9 ml of a 2 M sodium carbonate solution were heated under an inert gas atmosphere for 16 h. For the work-up the reaction mixture was poured into water, extracted with ethyl acetate, dried over sodium sulphate and concentrated in vacuo. Purification via column chromatography yielded 0.79 g (2.9 mmol, 95 %) of 2- [3-CHLORO-5- (TRIFLUOROMETHYL)-2-PYRIDINYLGANILINE [log P (pH 2.3) = 2. 79]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide In 1,4-dioxane; water for 6h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide In 1,4-dioxane; water for 2h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With caesium carbonate;palladium diacetate; In 1,4-dioxane; dichloromethane; water; ethyl acetate; | Step 1: Synthesis of 9-fluoro-6-phenanthridinamine To a solution of <strong>[60702-69-4]2-chloro-4-fluorobenzonitrile</strong> (1.0 g, 6.42 mmol), 2-aminophenylboronic acid pinacol ester (1.6 g, 7.1 mmol), palladium(II) acetate (0.07 g, 0.32 mmol), amantadine hydrochloride (0.24 g, 1.3 mmol) and cesium carbonate (4.6 g, 14.1 mmol) were added to dioxane previously deaerated with nitrogen and heated to reflux for 17 hours. After cooling, both distilled water and methylene chloride (50 mL) were added to the reaction mixture. The solvent layer was separated and concentrated to give a crude oil that was purified by column chromatography by first using 1:1 ethyl acetate and hexanes ratio followed by 4:1 ethyl acetate/hexanes as the eluants. The pure product was collected to give 9-fluoro-6-phenanthridinamine (42 g, 32 % Yield) whose NMR spectrum is consistent with the proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In tetrahydrofuran at 23℃; Inert atmosphere; | |
83% | In acetonitrile at 23℃; for 4h; Inert atmosphere; | |
83% | In acetonitrile at 23℃; for 4h; Inert atmosphere; |
83% | In acetonitrile at 23℃; for 4h; Inert atmosphere; | |
83% | In acetonitrile at 23℃; for 4h; Inert atmosphere; | |
81% | In dichloromethane at 20℃; | |
In acetonitrile at 23℃; for 4h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 2.1: (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate / tetrahydrofuran / 0.17 h / 20 °C / Molecular sieve; Inert atmosphere 2.2: 70 h / 20 °C / Molecular sieve; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium carbonate; In ethanol; at 80.0℃; for 3.0h; | Example 2a. 8-fluorophenanthridin-6-ol.A mixture of m<strong>[139911-28-7]ethyl 2-bromo-5-fluorobenzoate</strong> (0.250 g, 1.07 mmol), 2-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)aniline (0.235 g, 1.07 mmol), palladium acetate (2.4 mg, 0.01 eq.), dicyclohexyl(2',6'-dimethoxybiphenyl-2-yl)phosphine (8.81 mg, 0.021 mmol), and sodium carbonate (0.114 g, 1.073 mmol) in ethanol (5.4 mL) was heated to 80 C for 3 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was triturated with hexane, and isolated by vacuum filtration, washed with water, and dried to provide the title compound (0.15 g, 65% yield) which was used without further purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39%; 29% | General procedure: A solution of 3-phenyl sydnone (3, 100 mg, 1.0 equiv) in 4.0 mL p-xylene was added <strong>[41658-03-1]ethyl 3-bromopropynoate</strong> (120 mg, 1.05 equiv) and heated to reflux for 5 h. The residue was cooled down and added 2-aminophenylboronic acid pinacol ester (820 mg, 1.1 equiv), Pd(PPh3)4 (39 mg, 0.1 equiv), K2CO3 (2 mL, 2 M aqueous solution), and EtOH (4.0 mL). The reaction mixture was stirred at reflux for 24 h. When the reaction was completed, the reaction mixture was concentrated under reduced pressure to remove p-xylene and EtOH. The residue was added with 20 mL water, and extract with EtOAc (40 mL). The organic layer was filtered to remove the insoluble substances, then dried over MgSO4, filtered, and concentrated under reduced pressure. The residue solution was purified by column chromatography on silica gel to give the corresponding 2-arylpyrazolo[3,4-c]quinolin-4(5H)-one 1b-e and 2-arylpyrazolo[4,3-c]quinolin-4(5H)-one 2b-e products in 27-32% and 39-43% yields, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43%; 32% | General procedure: A solution of 3-phenyl sydnone (3, 100 mg, 1.0 equiv) in 4.0 mL p-xylene was added <strong>[41658-03-1]ethyl 3-bromopropynoate</strong> (120 mg, 1.05 equiv) and heated to reflux for 5 h. The residue was cooled down and added 2-aminophenylboronic acid pinacol ester (820 mg, 1.1 equiv), Pd(PPh3)4 (39 mg, 0.1 equiv), K2CO3 (2 mL, 2 M aqueous solution), and EtOH (4.0 mL). The reaction mixture was stirred at reflux for 24 h. When the reaction was completed, the reaction mixture was concentrated under reduced pressure to remove p-xylene and EtOH. The residue was added with 20 mL water, and extract with EtOAc (40 mL). The organic layer was filtered to remove the insoluble substances, then dried over MgSO4, filtered, and concentrated under reduced pressure. The residue solution was purified by column chromatography on silica gel to give the corresponding 2-arylpyrazolo[3,4-c]quinolin-4(5H)-one 1b-e and 2-arylpyrazolo[4,3-c]quinolin-4(5H)-one 2b-e products in 27-32% and 39-43% yields, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42%; 30% | General procedure: A solution of 3-phenyl sydnone (3, 100 mg, 1.0 equiv) in 4.0 mL p-xylene was added <strong>[41658-03-1]ethyl 3-bromopropynoate</strong> (120 mg, 1.05 equiv) and heated to reflux for 5 h. The residue was cooled down and added 2-aminophenylboronic acid pinacol ester (820 mg, 1.1 equiv), Pd(PPh3)4 (39 mg, 0.1 equiv), K2CO3 (2 mL, 2 M aqueous solution), and EtOH (4.0 mL). The reaction mixture was stirred at reflux for 24 h. When the reaction was completed, the reaction mixture was concentrated under reduced pressure to remove p-xylene and EtOH. The residue was added with 20 mL water, and extract with EtOAc (40 mL). The organic layer was filtered to remove the insoluble substances, then dried over MgSO4, filtered, and concentrated under reduced pressure. The residue solution was purified by column chromatography on silica gel to give the corresponding 2-arylpyrazolo[3,4-c]quinolin-4(5H)-one 1b-e and 2-arylpyrazolo[4,3-c]quinolin-4(5H)-one 2b-e products in 27-32% and 39-43% yields, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40%; 32% | General procedure: A solution of 3-phenyl sydnone (3, 100 mg, 1.0 equiv) in 4.0 mL p-xylene was added <strong>[41658-03-1]ethyl 3-bromopropynoate</strong> (120 mg, 1.05 equiv) and heated to reflux for 5 h. The residue was cooled down and added 2-aminophenylboronic acid pinacol ester (820 mg, 1.1 equiv), Pd(PPh3)4 (39 mg, 0.1 equiv), K2CO3 (2 mL, 2 M aqueous solution), and EtOH (4.0 mL). The reaction mixture was stirred at reflux for 24 h. When the reaction was completed, the reaction mixture was concentrated under reduced pressure to remove p-xylene and EtOH. The residue was added with 20 mL water, and extract with EtOAc (40 mL). The organic layer was filtered to remove the insoluble substances, then dried over MgSO4, filtered, and concentrated under reduced pressure. The residue solution was purified by column chromatography on silica gel to give the corresponding 2-arylpyrazolo[3,4-c]quinolin-4(5H)-one 1b-e and 2-arylpyrazolo[4,3-c]quinolin-4(5H)-one 2b-e products in 27-32% and 39-43% yields, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43%; 27% | General procedure: A solution of 3-phenyl sydnone (3, 100 mg, 1.0 equiv) in 4.0 mL p-xylene was added <strong>[41658-03-1]ethyl 3-bromopropynoate</strong> (120 mg, 1.05 equiv) and heated to reflux for 5 h. The residue was cooled down and added 2-aminophenylboronic acid pinacol ester (820 mg, 1.1 equiv), Pd(PPh3)4 (39 mg, 0.1 equiv), K2CO3 (2 mL, 2 M aqueous solution), and EtOH (4.0 mL). The reaction mixture was stirred at reflux for 24 h. When the reaction was completed, the reaction mixture was concentrated under reduced pressure to remove p-xylene and EtOH. The residue was added with 20 mL water, and extract with EtOAc (40 mL). The organic layer was filtered to remove the insoluble substances, then dried over MgSO4, filtered, and concentrated under reduced pressure. The residue solution was purified by column chromatography on silica gel to give the corresponding 2-arylpyrazolo[3,4-c]quinolin-4(5H)-one 1b-e and 2-arylpyrazolo[4,3-c]quinolin-4(5H)-one 2b-e products in 27-32% and 39-43% yields, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With potassium phosphate monohydrate;bis-triphenylphosphine-palladium(II) chloride; In water; toluene; for 15.5h;Inert atmosphere; | 2-Bromo-5-methoxybenzonitrile (1.32 g, 6.23 mmol), 2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (1.36 g, 6.23 mmol), bis(triphenylphosphine)palladiumdichloride (0.437 g, 0.623 mmol) and potassium phosphate monohydrate (4.30 g, 18.68 mmol) were added to toluene (30 mL) and water (3 mL). The reaction mixture was degassed with bubbled nitrogen gas for 30 minutes before being refluxed under nitrogen for 15 h. After cooling, the reaction mixture was filtered through Celite and the organic layer was extracted with ethyl acetate. After removal of the solvents, the crude material was triturated with 40 mL of DCM followed by 50 mL of hexanes to give 8- methoxyphenanthridin-6-amine (0.95g, 68%) as a light yellow solid. The product was confirmed by GC/MS and NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | General procedure: To a 2-5 mL capacity microwave vial was charged <strong>[57486-69-8]methyl 2-(2-bromophenyl)acetate</strong> (0.100g, 0.43 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.115 g, 0.523 mmol)and cesium carbonate (0.280 g, 0.86 mmol) in anhydrous 1,2-dimethoxy ethane (4 mL). Themixture was stirred and degassed with argon for 5 min. To this mixture was added Pd(PPh3)4(25 mg, 0.021 mmol) under argon atmosphere, and purged for 2 min. The tube was sealedand irradiated in microwave at 125 C for 0.5 h (This is the internal temperature of reactionmixture and monitored on the screen through a sensor). The vial was cooled to 0C over aperiod of 15 min, followed by addition of 1M potassium tert-butoxide (0.65 mL, 0.65 mmol)solution in THF. The resulting mixture was stirred for 10 minutes and quenched withsaturated ammonium chloride solution. The mixture was diluted with ethyl acetate (30 mL)and washed with water and brine. The organic layer was dried over anhydrous sodiumsulfate, filtered and concentrated. The residue obtained was purified by flash columnchromatography by eluting with gradient of 2-20% ethyl acetate in hexane to afford the 5Hdibenzo[b,d]azepin-6(7H)-one (4) as off white solid (0.075 g, 82%).1H NMR (400 MHz, CDCl3) delta 7.66-7.64 (d, 1H, J = 8 Hz), 7.59-7.56 (m, 2H), 7.42-7.38 (m, 4H), 7.30 (t, 1H, J = 8 Hz), 7.09-7.07 (d, 1H, J = 8 Hz), 3.55-3.48 (m, 2H); LC-MS m/z 210.07 (M+H+); Purity: 99.69% (AUC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In water; N,N-dimethyl-formamide; at 80℃; for 1h;Inert atmosphere; | Step 1:To a stirred solution of tert-butyl hydrazinecarboxylate 22b (50 g, 412.37 mmol) and 2,5-dimethoxytetrahydrofuran 22a (54.5 g, 412.37 mmol) in dioxane (300 mL) was added aqueous hydrochloric acid (5 mL, 2N). The reaction was set up using a dean-stark apparatus and heated at 90 C for 20 h. Reaction mixture was cooled to 20 C, neutralized with saturated sodium bicarbonate (18 mL) and filtered to remove inorganics. The filtrate was concentrated in vacuum and triturated with ether. The solid obtained was collected by filtration to furnish on drying tert-butyl lH-pyrrol-l-ylcarbamate 22c (43 g, 57.2%) as a yellow brown solid. 1H NMR (300 MHz, CD3OD) ? 6.62 (t, J= 2.3, 2H), 6.02 (t, J= 2.3, 2H), 1.48 (s, 9H); MS (ES+): 181.1 (M _1). Analysis: Calculated for C9Hi4N202: C, 59.32; H, 7.74; N, 15.37. Found: C, 59.32; H, 7.65; N, 15.02. Step 2:To a stirred solution of tert-butyl lH-pyrrol-l-ylcarbamate 22c (40 g, 219.52 mmol), in acetonitrile (350 mL) was added chlorosulfonyl isocyanate (32.62 g, 230.50 mmol) slowly at 0 C and continued stirring at 0 C for 30 min. To the solution N, N-dimethyl formamide (40 mL) was added below 5 C and continued stirring at 0 C for 1 hr. The reaction mixture was poured into a mixture of crushed ice (1 L) and ethyl acetate (1 L). The layers were separated and the organic layer was washed with water (500 mL), brine (250 mL), dried and concentrated in vacuum to furnish crude (43 g) product. The crude was purified by flash chromatography (silica gel, eluting with ethyl acetate in hexane0-50%) to afford pure tert-butyl 2-cyano-lH-pyrrol-l-ylcarbamate 22d (30 g, 66 %>) as a colorless solid. 1H NMR (300 MHz, DMSO-d6) ? 10.80 (s, 1H, D20 exchangeable), 7.23 (dd, J= 1.7, 2.9, 1H), 6.94 (dd, J= 1.7, 4.3, 1H), 6.20 (dd, J= 2.9, 4.3, 1H), 1.45 (s, 9H). Analysis: Calculated for Ci0Hi3N3O2: C, 57.95; H, 6.32; N, 20.27. Found: C, 58.02; H, 6.45; N, 20.18. Step 3:To a stirred solution of tert-butyl 2-cyano-lH-pyrrol-l-ylcarbamate 22d (5 g, 24.12 mmol) in ethyl alcohol (100 mL) was added concentrated aqueous ammonium hydroxide solution (50 mL) at 20 C followed by hydrogen peroxide (7.4 mL, 72.38 mmol, 30 % in water) slowly at 20 C and stirred at the same temperature for 16 h. Reaction mixture was concentrated in vacuum and diluted with ethyl acetate (150 mL), washed with water (2 x 50 mL). The aqueous layer was extracted with ethyl acetate (150 mL). The combined ethyl acetate layers were washed with water (100 mL), brine (50 mL), dried, filtered, and concentrated in vacuum. The residue obtained was crystallized from diisopropyl ether and hexane to afford tert-butyl 2-carbamoyl-lH-pyrrol-l-ylcarbamate 22e (4.0 g, 73.6%) as a colorless solid. 1H NMR (300 MHz, DMSO-d6) ? 9.89 (s, 1H, D20 exchangeable), 7.31 (d, J = 38.5, 1H), 6.84 (dd, J= 1.9, 2.8, 2H, lH is D20 exchangeable), 6.76 (dd, J = 1.9, 4.2, 1H), 5.97 (dd, J= 2.8, 4.2, 1H), 1.40 (s, 9H); Analysis: Calculated for Ci0Hi5N3O3: C, 53.32; H, 6.71 ; N, 18.65. Found: C, 53.40; H, 6.74; N, 18.55. Step 4:To a solution of tert-butyl 2-carbamoyl-lH-pyrrol-l-ylcarbamate 22e (2g, 8.87 mmol) in dichloromethane (15 mL) was added trifluoro acetic acid (15 mL) at 20 C and stirred for 30 min. The reaction mixture was concentrated to dryness to remove excess trifluoroacetic acid and diluted with dichloromethane. Triethylorthoformate (30 mL) was added to the residue and was heated to 79 C overnight. Reaction mixture was concentrated to dryness and triturated with hexanes, the solid obtained was collected by filtration dried in vacuum to give crude pyrrolo[l ,2-f][l ,2,4]triazin-4-ol 22f (1.1 g, 91%) as a dark brown solid. 1H NMR (300 MHz, DMSO-d6) ? 11.63 (s, 1H, D20 exchangeable), 7.83 (d, J= 4.0, 1H), 7.59 (dd, J= 1.7, 2.6, 1H), 6.89 (dd, J= 1.6, 4.3, 1H), 6.54 (dd, J = 2.7, 4.3, 1H); MS (ES+): 136.2 (M + l). Step 5:The stirred solution of pyrrolo[l ,2-f][l ,2,4]triazin-4-ol 22f (1 g, 7.40 mmol), benzyltriethylammonium chloride (3.29 g, 14.80 mmol), and N,N-dimethylaniline (1.35 g, 1 1.10 mmol) in acetonitrile (25 mL) was heated to 80 C and at this temperature phosphorous oxy chloride (6.88 g, 44.40 mmol) was added and stirred at 80 C for 16 h. The reaction was concentrated to remove acetonitrile and phosphorus oxy chloride. The reaction was quenched by adding ice water (20 mL) and extracted with ethyl acetate (2 x 100 mL). The ethyl acetate extracts were combined washed with hydrochloric acid (1 N, 30 mL), water (50 mL), saturated sodium bicarbonate (1 x 20 mL), water (50 mL), brine (20 mL) dried and concentrated. The crude residue was purified by flash chromatography (silica gel, eluting with ethyl acetate in hexanes (0 to 5 %)) to furnish pure4-chloropyrrolo[l,2-fJ[l,2,4]triazine 22g (0.7 g, 61.6 %) as a colorless oil, which solidified on standing in refrigerator. 1H NMR (300 MHz, DMSO-d6) ? 8.44 (s, 1H), 8.27 (dd, J = 1.5, 2.5, 1H), 7.12 (qd, J= 2.0, 4.6, 2H). Step 6:A solution of 2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (10m) (2.3 g, 9.8 ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 75 - 100℃; for 8.08333h;Inert atmosphere; | General procedure: A solution of 2 M Na2CO3 (10 mL) was added under nitrogen to a 2-bromoaniline (10 mmol) in 60 mL dioxane. After 5 min stirring at 75 C, Pd[P(C6H5)3]4 was added followed by (10 mmol) of a 2-cyanophenylboronic acid pinacol ester. The reaction was stirred 8 h at 100 C. After cooling to rt the mixture was vacuum concentrated to half of its initial volume and extracted with CH2Cl2 (30 mL) and water (30 mL). The aqueous phase was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The solid crystallized upon concentration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 75 - 100℃; for 8.08333h; Inert atmosphere; | 4.1.1.1 Suzuki coupling conditions General procedure: A solution of 2 M Na2CO3 (10 mL) was added under nitrogen to a 2-bromoaniline (10 mmol) in 60 mL dioxane. After 5 min stirring at 75 °C, Pd[P(C6H5)3]4 was added followed by (10 mmol) of a 2-cyanophenylboronic acid pinacol ester. The reaction was stirred 8 h at 100 °C. After cooling to rt the mixture was vacuum concentrated to half of its initial volume and extracted with CH2Cl2 (30 mL) and water (30 mL). The aqueous phase was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The solid crystallized upon concentration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 75 - 100℃; for 8.08333h;Inert atmosphere; | General procedure: A solution of 2 M Na2CO3 (10 mL) was added under nitrogen to a 2-bromoaniline (10 mmol) in 60 mL dioxane. After 5 min stirring at 75 C, Pd[P(C6H5)3]4 was added followed by (10 mmol) of a 2-cyanophenylboronic acid pinacol ester. The reaction was stirred 8 h at 100 C. After cooling to rt the mixture was vacuum concentrated to half of its initial volume and extracted with CH2Cl2 (30 mL) and water (30 mL). The aqueous phase was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The solid crystallized upon concentration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 75 - 100℃; for 8.08333h;Inert atmosphere; | General procedure: A solution of 2 M Na2CO3 (10 mL) was added under nitrogen to a 2-bromoaniline (10 mmol) in 60 mL dioxane. After 5 min stirring at 75 C, Pd[P(C6H5)3]4 was added followed by (10 mmol) of a 2-cyanophenylboronic acid pinacol ester. The reaction was stirred 8 h at 100 C. After cooling to rt the mixture was vacuum concentrated to half of its initial volume and extracted with CH2Cl2 (30 mL) and water (30 mL). The aqueous phase was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The solid crystallized upon concentration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 75 - 100℃; for 8.08333h; Inert atmosphere; | 4.1.1.1 Suzuki coupling conditions General procedure: A solution of 2 M Na2CO3 (10 mL) was added under nitrogen to a 2-bromoaniline (10 mmol) in 60 mL dioxane. After 5 min stirring at 75 °C, Pd[P(C6H5)3]4 was added followed by (10 mmol) of a 2-cyanophenylboronic acid pinacol ester. The reaction was stirred 8 h at 100 °C. After cooling to rt the mixture was vacuum concentrated to half of its initial volume and extracted with CH2Cl2 (30 mL) and water (30 mL). The aqueous phase was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The solid crystallized upon concentration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 8.08 h / 75 - 100 °C / Inert atmosphere 2: iron; hydrogenchloride; ammonium chloride / ethanol; water / 3 h / 55 - 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 75 - 100℃; for 8.08333h;Inert atmosphere; | General procedure: A solution of 2 M Na2CO3 (10 mL) was added under nitrogen to a 2-bromoaniline (10 mmol) in 60 mL dioxane. After 5 min stirring at 75 C, Pd[P(C6H5)3]4 was added followed by (10 mmol) of a 2-cyanophenylboronic acid pinacol ester. The reaction was stirred 8 h at 100 C. After cooling to rt the mixture was vacuum concentrated to half of its initial volume and extracted with CH2Cl2 (30 mL) and water (30 mL). The aqueous phase was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The solid crystallized upon concentration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 75 - 100℃; for 8.08333h; Inert atmosphere; | 4.1.1.1 Suzuki coupling conditions General procedure: A solution of 2 M Na2CO3 (10 mL) was added under nitrogen to a 2-bromoaniline (10 mmol) in 60 mL dioxane. After 5 min stirring at 75 °C, Pd[P(C6H5)3]4 was added followed by (10 mmol) of a 2-cyanophenylboronic acid pinacol ester. The reaction was stirred 8 h at 100 °C. After cooling to rt the mixture was vacuum concentrated to half of its initial volume and extracted with CH2Cl2 (30 mL) and water (30 mL). The aqueous phase was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The solid crystallized upon concentration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With [1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride; sodium carbonate; In ethanol; toluene; at 100℃; for 3h;Sealed tube; | A mixture of <strong>[5177-27-5]2,4-dichloropyrimidin-5-amine</strong> (246 mg, 1.5 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine (219 mg, 1.0 mmol), Pd(dppb)Cl2 (60 mg, 0.1 mmol) and Na2CO3 (4 mL, 1.0 M solution) in toluene/EtOH (2.0 mL/3.0 mL) was heated at 100 C. in a seal tube for 3 h. The reaction was then filtered through celite, eluted with dichloromethane, washed by brine, and concentrated in vacuo. The residue was then purified by silica gel chromatography with 3.5 N ammonia in MeOH solution: dichloromethane to give 4-(2-aminophenyl)-2-chloropyrimidin-5-amine (158 mg, 48%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In dimethyl sulfoxide at 120℃; for 8h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With dichloro[1,1?-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P?]palladium; sodium carbonate; In tetrahydrofuran; water; at 20 - 50℃; for 64.0h;Inert atmosphere; | Example 54 tert-butyl (2R,6S,13aS,14aR,16aS,Z)-14a-(cyclopropylsulfonylcarbamoyl)-5,16-dioxo-2-(thiazolo[4,5-c]quinolin-4-yloxy)-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-ylcarbamate A mixture of <strong>[913836-22-3]5-bromothiazole-4-carboxylic acid methyl ester</strong> (0.521 g, 2.35 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.514 g. 2.35 mmol), 1,1'-bis(di-t-butylphosphino)ferrocene palladium chloride (0.060 g, 0.094 mmol), and sodium carbonate (1.17 mL of 2M aqueous solution) in tetrahydrofuran (12 mL) was stirred under nitrogen at rt for 48 h. The reaction mixture was then heated at 50 C. for an additional 16 h. The reaction mixture was then cooled to rt, diluted with dichloromethane (120 mL) and dimethylformamide (40 mL) and washed with water (20 mL). The resulting solid was isolated by vacuum filtration to provide the title compound (0.251 mg, 53% yield, thiazolo[4,5-c]quinolin-4(5H)-one). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With triethylamine In dichloromethane at 4 - 20℃; for 18h; | N4,N4'-bis(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1’-biphenyl]-4,4’-dicarboxamide (3cb) General procedure: After cooling a solution of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1c) (438.2 mg, 2.00 mmol)and CH2Cl2 (4.348 mL) at 4.0 °C, Et3N (415.9 μL, 3.00 mmol) and terephthaloyl chloride (2a) (203.0 mg,1.00 mmol) were added. The mixture was stirred at room temperature for 18 h and then water (ca. 100mL) was added. The resulting mixture was extracted with AcOEt (x3) and combined organic extractcontaining yellow solid material was filtered. The separated insoluble material was washed with AcOEt togive the desired product (3ca) (511.9 mg, 90% yield) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With triethylamine In dichloromethane at 4 - 20℃; for 18h; | N1,N8-bis(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)octanediamide (3cd) General procedure: After cooling a solution of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1c) (438.2 mg, 2.00 mmol)and CH2Cl2 (4.348 mL) at 4.0 °C, Et3N (415.9 μL, 3.00 mmol) and terephthaloyl chloride (2a) (203.0 mg,1.00 mmol) were added. The mixture was stirred at room temperature for 18 h and then water (ca. 100mL) was added. The resulting mixture was extracted with AcOEt (x3) and combined organic extractcontaining yellow solid material was filtered. The separated insoluble material was washed with AcOEt togive the desired product (3ca) (511.9 mg, 90% yield) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 120℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,2-dimethoxyethane; water / 16 h / 120 °C 2.1: tert.-butylnitrite / 1,2-dichloro-ethane / 0.17 h / Sealed tube 2.2: 24 h / 20 °C / Sealed tube; Irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In ethanol; at 20℃; | Step A: To a mixture of 5a (0.44 g, 2.0 mmol) and EtOH (9.0 mL)was added 1H-benzotriazole-1-methanol (0.30 g, 2.0 mmol). After stirring at room temperature overnight, the reaction mixture was concentrated in vacuo and the obtained residue was triturated with hexane. The resulting precipitate was collected by filtration to give N-(1H-Benzotriazol-1-ylmethyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.59 g, 84%) as a brown solid. 1HNMR (CDCl3) d: 8.03 (1H, d, J = 8.2 Hz), 7.67 (1H, d, J = 8.2 Hz),7.62 (1H, dd, J = 7.4, 1.6 Hz), 7.44-7.40 (1H, m), 7.33-7.28 (2H,m), 7.09 (1H, t, J = 7.2 Hz), 7.02 (1H, d, J = 8.2 Hz), 6.73 (1H, td,J = 7.4, 0.8 Hz), 6.16 (2H, d, J = 7.4 Hz), 1.37 (12H, s). MS (ESI-) m/z:349 (MH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.4% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In ethanol; water; toluene; at 120℃; for 5.0h; | 1) Preparation of compound 1-1 After introducing compoundA(36.0g, 152.3mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)aniline (40g, 182.7mmol), tetrakis(triphenylphosphine)palladium (5.28g, 4.6mmol), cesium carbonate (124.0g, 380.6mmol), toluene (760mL), EtOH (190mL), and distilled water (190mL) into a reaction vessel, the mixture was stirred at 120°C for 5 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The obtained organic layer was dried with magnesium sulfate and the solvent was removed therefrom by a rotary evaporator. The products were purified by column chromatography to obtain compound1-1(19.3g, yield: 50.4percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In tetrahydrofuran; at 60℃; for 4h;Inert atmosphere; | Into a 2-L 3-necked round- bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-(3- bromophenoxy)propanoic acid (73 g, 297.87 mmol, 1.00 equiv), tetrahydrofuran (750 mL), 2- (tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (57 g, 260.17 mmol, 1.30 equiv), 1M K3P04 (307 mL, 3.00 equiv), and Pd(dppf)Cl2 (25 g, 34.17 mmol, 0.10 equiv). The resulting solution was stirred for 4 h at 60C in an oil bath, then extracted with of ethyl acetate (2x500 mL). The combined organic layers were washed with of water (1x500 mL) and of brine (1x500 mL), then dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting residue was purified on a silica gel column eluting with ethyl acetate/hexane (1 : 10) to give the title compound | |
With potassium phosphate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; In tetrahydrofuran; at 60℃; for 4h;Inert atmosphere; | Into a 2-L 3-necked round bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-(3- bromophenoxy)propanoic acid (73 g, 297.87 mmol, 1.00 equiv), tetrahydrofuran (750 mL), 2- (tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (57 g, 260.17 mmol, 1.30 equiv), 1M K3P04 (307 mL, 3.00 equiv), and Pd(dppf)C12 (25 g, 34.17 mmol, 0.10 equiv). The resulting solution wasstirred for 4 h at 60C in an oil bath, then extracted with of ethyl acetate (2x500 mL). The combined organic layers were washed with of water (1x500 mL) and of brine (1x500 mL), then dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting residue was purified on a silica gel column eluting with ethyl acetate/hexane (1:10) to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With triethylamine In dichloromethane at 4 - 20℃; for 18h; | N1,N3,N5-tris(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzene-1,3,5-tricarboxamide (3c) After cooling a solution of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1c) (657.3 mg, 3.00 mmol) and CH2Cl2 (4.348 mL) at 4.0C with stirring under atmospheric conditions, Et3N (623.8 mL, 4.50 mmol) and 1,3,5-benzenetricarbonyl chloride (2)(265.5 mg, 1.00 mmol) were added. The resulting mixture was stirred at room temperature for 18 h and then water (ca. 100 mL) was added. The mixture was extracted with AcOEt (x3) and the combined organic extract was dried over anhydrous Na2SO4. After filtration, the solvents were evaporated under reduced pressure. The obtained crude material was washed with AcOEt/n-hexane to give the desired product (3c) (292.6 mg, 36% yield) as a white solid. The structure of the product was established by spectroscopic data shown below.14 Mp 243-245C; IR (KBr) 3457 (NH), 1684 cm1 (C D O); FAB-MS(positive) m/z 814 (MCH)C. HRMS (FAB) Calcd for C45H55B3N3O9C: m/z 814.4212(MCH)C. Found: 814.4209; 1H-NMR (DMSO-d6) d 1.26 (36H, s, CH3), 7.23 (3H, dd,J D 6.6 Hz, 7.8 Hz, Ar H-4, in B-C6H4-N), 7.45-7.52 (3H, m, Ar H-5, in B-C6H4-N),7.58-7.66 (3H, m, Ar H-3, in B-C6H4-N), 7.84 (3H, d, J D 7.8 Hz, Ar H-6, in B-C6H4-N), 8.87 {3H, s, Ar H-2, H-4, H-6 in C6H3-[C( D O)]3}, 11.41 (3H, s, NH); 13C-NMR(DMSO-d6) d 25.2 (CH3), 82.3 (B-O-C-C-O-B), 119.0 (Ar C-6 in B-C6H4-N), 124.9 (ArC-4 in B-C6H4-N), 130.0, 130.3 {Ar C-2 in C6H3-[C( D O)]3 or Ar C-5 in B-C6H4-N},134.2 (Ar C-3 in B-C6H4-N), 134.4 {Ar C-1 in C6H3-[C( D O)]3}, 141.0 (Ar C-1 in BC6H4-N), 163.9 (C D O). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In ethanol; water; toluene; for 24h;Reflux; | 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline is dissolved in toluene and placed in a two-neck flask.Add Tripotassium phosphate Pd (PPh3) 2Cl2 and Ethanol dissolved in water. After 5 minutes, add <strong>[42872-73-1]2-bromo-4-methylbenzonitrile</strong>. Allow to reflux for 24 hours. When the reaction is complete, extract with CH2Cl2. Purification by silica gel column (yield: 70%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In ethanol; water; toluene; for 24.0h;Reflux; | 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline is dissolved in toluene and placed in a two-neck flask.Add Tripotassium phosphate, Pd (PPh3) 2Cl2 and Ethanol dissolved in water. After 5 minutes, add 2-bromo-4- (trifluoromethyl) benzonitrile. Allow to reflux for 24 hours. When the reaction is complete, extract with CH2Cl2. Purification by silica gel column (yield: 73%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In ethanol; water; toluene for 24h; Reflux; | 6.1.1-6 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline is dissolved in toluene and placed in a two-neck flask. Add Tripotassium phosphate, Pd (PPh3) 2Cl2 and Ethanol dissolved in water. After 5 minutes, add 2-bromo-4-fluorobenzonitrile. Allow to reflux for 24 hours. When the reaction is complete, extract with CH2Cl2. Purification by silica gel column (yield: 72%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere; | <strong>[601-88-7]2,6-dichloronitrobenzene</strong> (6.5 g 34 mmol) was combined with 2-(4,4,5,5-Tetramethyl-1 ,3,2- dioxaborolan-2-yl)aniline (5 g, 22.6 mmol) in the presence of Pd(PPh3)4 (0.5 g, 0.45 mmol) and K2C03 (6.25 g, 45 mmol) in Dioxane/water (100 mL, 4:1) and the resulting mixture wasdegassed with N2. The reaction was stirred at an oil bath temperature of 90 °C overnight. The solvent was evaporated under reduced pressure and the crude residue dissolved in CH2CI2, washed with water and dried over anhydrous MgSO4. The product was purified by chromatography on silica using 20 percent EtOAc in heptane as eluant. Compound 13 (5 g, 90 percent yield) was thus obtained. The product was confirmed by HPLC MS mlz 249 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With allylchloro[1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidene]palladium(II); barium(II) hydroxide; In isopropyl alcohol; at 80℃; for 6h; | 100ml three-neck eggplant flask fully dried2- (4,4,5,5-tetramethyl-1,3,2-dioxabolan-2-yl) aniline (manufactured by Tokyo Chemical Industry Co., Ltd.) (with condenser, three-way cock and magnetic stir bar)2.41 g (11 mmol),1.61 g (10 mmol) of <strong>[53145-38-3]2-chloro-6-fluoroanisole</strong>,1,3-bis- (2,6-diisopropylphenyl) imidazolium- (allyl) -palladium (II) -chloride(Sigma Aldrich Japan Co., Ltd.)0.029 g (0.05 mmol),Barium hydroxide octahydrate (manufactured by Wako Pure Chemical Industries, Ltd.)4.73 g (15 mmol) was added,Dissolved in 50 mL of isopropyl alcohol,The reaction was performed at 80 C. for 6 hours.After the reaction, the solid residue is removed by filtration,The solvent was distilled off under reduced pressure to obtain a crude product.Crude product is silica gel column chromatograph(Eluent; hexane / ethyl acetate = 9/1)1.37 g (63%, white solid) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: 1,3,5-trisbromobenzene; 2-anilineboronic acid pinacol ester With potassium carbonate In ethanol; water; toluene for 0.416667h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 90℃; for 5.16667h; Sealed tube; Inert atmosphere; | 1 (1) Preparation steps of 5'-bromo-[1,1':3',1"-terphenyl]-2,2"-diamine:In a 500ml reaction eggplant-shaped bottleAdd 5.0g of tribromobenzene,6.7g 2-aminophenylboronic acid pinacol ester, 13.2g potassium carbonate, 100ml toluene,28ml of ethanol and 28ml of water, then the reaction mixture in the bottle was bubbled with nitrogen for 25min; then 923.0mg of tetratriphenylphosphine palladium was added to the reaction system,Then continue to bubble the reaction mixture for 10 min; under sealed conditions, the reaction mixture was heated to 90 °C while stirring with a magnet for 5 h; after the reaction was completed, the reaction liquid was returned to room temperature, poured into water and extracted with dichloromethane for three times Collect the organic phase over and over; finally remove the solvent and separate it by column chromatography to obtain 4.1g of 5'-bromo-[1,1':3',1"-terphenyl]-2,2"-diamine, White solid, yield 76%. |
76% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 5h; Schlenk technique; Inert atmosphere; | |
56% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 5h; Schlenk technique; Inert atmosphere; |
56% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 5h; | 1 (1) Preparation steps of 5'-bromo- [1,1 ': 3', 1 ″ -terphenyl] -2,2 ″ -diamine: In a 500ml reaction eggplant-shaped bottle, add 5g mesotribromobenzene, 6.7g 2-aminophenylboronic acid pinacol ester, 13.2g potassium carbonate,100ml toluene, 28ml ethanol and 28ml water,Then the reaction mixture in the bottle was bubbled with nitrogen for 25 min; then 923 mg of palladium tetratriphenylphosphine was added to the reaction system, and then the reaction mixture was bubbled for 10 min; under sealed conditions,The reaction mixture was heated to 90 ° C,At the same time, stir with a magnet for 5h; after the reaction,The reaction solution was returned to room temperature, poured into water and extracted three times with dichloromethane, and the organic phase was collected;Finally, the solvent was removed, and 3.03g of 5'-bromo- [1,1 ': 3', 1 ″ -terphenyl] -2,2 ″ -diamine was isolated by column chromatography, a white solid with a yield of 56 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.8% | With 5%-palladium/activated carbon; hydrogen; In ethyl acetate; at 80℃; for 4h;Inert atmosphere; | According to Example 2, <strong>[190788-59-1]2-nitrophenylboronic acid pinacol ester</strong> was obtained and subjected to hydrogenation reaction to prepare 2-aminophenylboronic acid pinacol ester.Put <strong>[190788-59-1]2-nitrophenylboronic acid pinacol ester</strong> (19.9g, 0.8mol), 5% palladium carbon (1.9g) and 202g ethyl acetate into a 500mL hydrogenation kettle,Nitrogen was replaced three times, stirring was started and the temperature was raised to 80 C.Keep at 80 C and stir for 4.0h. The detection found that the raw materials reacted completely, and the reaction basically had no by-products formed.Stop the reaction, lower the temperature to room temperature, filter with suction, and spin the filtrate,The n-heptane / dichlorohexane (volume ratio 15: 1) was recrystallized to obtain 17.1 g of 2-aminophenylboronic acid pinacol ester with a yield of 97.3%.Replace the ethyl acetate solvent with tetrahydrofuran for hydrogenation,Recrystallization yielded 16.7 g of 2-aminophenylboronic acid pinacol ester with a yield of 95.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 110℃; for 6h; | M1-A (0.08mol, 1eq), o-aminophenyl boronic acid pinacol ester (0.1mol, 1.2eq), potassium carbonate (0.12mol, 1.5eq), tetrakis (triphenylphosphine) palladium (0.0008mol, 0.01 eq), dioxane (250 mL) and water (40 mL) were added to a three-necked flask. The oil bath was heated to 110°C for 6 hours, and TLC monitored the completion of the reaction. The reaction solution was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure. The crude product was purified by column chromatography to obtain intermediate M1-B. | |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 110℃; for 6h; | M-A (0.08mol, leq), pinacol anthranilate (0.1mol, 1.2eq),Potassium carbonate (0.12mol, 1.5eq), tetrakis (triphenylphosphine) palladium (0.0008mol, 0.01eq),Dioxane (250ml) and water (40ml) were added to a three-necked flask.The oil bath was heated to 110°C for 6 hours, and TLC monitored the completion of the reaction.Cool the reaction solution to room temperature,The crude product obtained by rotary evaporation under reduced pressure to remove the solvent was purified by column chromatography to obtain intermediate M-B. | |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 110℃; for 6h; | Combine MA (0.08mol, 1eq), anthranilate pinacol ester (0.1mol, 1.2eq), potassium carbonate (0.12mol, 1.5eq), tetrakis (triphenylphosphine) palladium (0.0008mol, 0.01eq) , Dioxane (250mL) and water (40mL) were added to the three-necked flask. The oil bath was heated to 110°C to react for 6 hours, and the completion of the reaction was monitored by thin layer chromatography (TLC). The reaction solution was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure. The crude product was purified by column chromatography to obtain Intermediate M-B. |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 110℃; for 6h; | Combine MA (0.08mol, 1eq), anthranilate pinacol ester (0.1mol, 1.2eq), potassium carbonate (0.12mol, 1.5eq), tetrakis (triphenylphosphine) palladium (0.0008mol, 0.01eq) , Dioxane (250ml) and water (40ml) were added to the three-necked flask. The oil bath was heated to 110°C for 6 hours, and TLC monitored the completion of the reaction. The reaction solution was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure. The crude product obtained was purified by column chromatography to obtain Intermediate M-B. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis-(triphenylphosphine)-palladium / tetrahydrofuran; water monomer / 12 h / Inert atmosphere; Schlenk technique; Reflux 2: sodium tertiary butoxide; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butylphosphonium hydrogen tetrafluoroborate / toluene / Inert atmosphere; Schlenk technique; Reflux |
Tags: 191171-55-8 synthesis path| 191171-55-8 SDS| 191171-55-8 COA| 191171-55-8 purity| 191171-55-8 application| 191171-55-8 NMR| 191171-55-8 COA| 191171-55-8 structure
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