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CAS No. : | 182163-96-8 | MDL No. : | MFCD01075676 |
Formula : | C9H13BO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RULQUTYJXDLRFL-UHFFFAOYSA-N |
M.W : | 212.01 | Pubchem ID : | 2734390 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 55.74 |
TPSA : | 68.15 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.07 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.74 |
Log Po/w (WLOGP) : | -0.61 |
Log Po/w (MLOGP) : | -0.5 |
Log Po/w (SILICOS-IT) : | -0.69 |
Consensus Log Po/w : | -0.21 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.65 |
Solubility : | 4.72 mg/ml ; 0.0223 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.75 |
Solubility : | 3.77 mg/ml ; 0.0178 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.68 |
Solubility : | 4.44 mg/ml ; 0.0209 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.46 |
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 |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In acetonitrile for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In acetonitrile for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 80℃; | Synthesis of 1-isopropyl-3-(3,4,5-trimethoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA64); A solution of 3,4,5-trimethoxyphenylboronic acid (123 mg, 0.58 mmol) in EtOH (3.3 ml) was added to a solution of <strong>[862730-04-9]3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine</strong> (70 mg, 0.23 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by silica gel column chromatography [MeOH-CH2Cl2, 2:98] to yield BA64 (70 mg, 89% yield). ESI-MS (M+H)+ m/z calcd 344.1, found 344.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate;tris-(o-tolyl)phosphine; bis(dibenzylideneacetone)-palladium(0); In 1,2-dimethoxyethane; water; at 85℃; | Example 3 ; Preparation of (4-fluoro-phenyl)-[3-(3,4,5-trimethoxy- phenyl)-pyrazolo[1 ,5-a]pyrimidin-5-yl]-amineExample 3a Preparation of 5-chloro-3-(3,4,5-trimethoxy-phenyl)-pyrazolo[1 ,5- a]pyrimidineA mixture of Intermediate A (1 g, 4.3 mmol), 3,4,5-trimethoxyphenyl boronic acid (1.62 g, 7.66 mmol), Pddba2 (99 mg, 0.17 mmol), P(OToI)3 (157 mg, 0.12 mmol), saturated aqueous sodium hydrogen carbonate solution (6.7 mL) and DME (31 mL) was purged with argon and heated at 85 0C over night. On cooling, the mixture was poured onto saturated aqueous ammonium chloride solution and extracted with EtOAc. The combined organic layers were washed with brine, dried, concentrated in vacuo and the residue purified by chromatography to give a mixture of 5-chloro-3-(3,4,5-trimethoxy-phenyl)- <n="67"/>pyrazolo[1 ,5-a]pyrimidine and 3-bromo-5-(3,4,5-trimethoxy-phenyl)- pyrazolo[1 ,5-a]pyrimidine, which was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
P.47 Synthesis of ethyl 5-(3,4,5-trimethoxyphenyl)nicotinate: PREPARATION EXAMPLE 47 Synthesis of ethyl 5-(3,4,5-trimethoxyphenyl)nicotinate: 3,4,5-Trimethoxyphenylboronic acid (6.36 g) and ethyl 5-chloronicotinate (6.90 g) were reacted in the same manner as in Preparation Example 1 to obtain the title compound. Yield: 7.19 g (76%). 1H-NMR (400 MHz, CDCl3) δ: 1.44 (t, 3H, J=7.1 Hz), 3.91 (s, 3H), 3.95 (s, 6H), 4.46 (q, 2H, J=7.1 Hz), 6.79(s, 2H), 8.44 (t, 1H, J=2.1 Hz), 8.96 (d, 1H, J=2.1 Hz), 9.18 (d, 1H, J=1.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
PREPARATION EXAMPLE 67 Synthesis of 4-methyl-6-(3,4,5-trimethoxyphenyl)-pyrimidine: <strong>[3435-25-4]4-Chloro-6-methylpyrimidine</strong> (913 mg) and 3,4,5-trimethoxyphenylboronic acid (2.73 g) were reacted in the same manner as in Preparation Example 1 to obtain the title compound. Yield: 920 mg (50%). 1H-NMR (400 MHz, CDCl3) delta: 2.51 (s, 3H), 3.84 (s, 3H), 3.88 (s, 6H), 7.25 (s, 2H), 7.44 (d, 1H, J=0.6 Hz), 8.02 (d, 1H, J=1.2 Hz). | ||
PREPARATION EXAMPLE 49 Synthesis of 4-Methyl-6-(3,4,5-trimethoxyphenyl)-pyrimidine <strong>[3435-25-4]4-Chloro-6-methylpyrimidine</strong> (913 mg) and 3,4,5-Trimethoxyphenylboronic acid (2.73 g) were reacted in the same manner as in Preparation Example 1 to obtain the title compound. Yield: 920 mg (50%). 1H-NMR (400 MHz, CDCl3) delta: 2.51 (s, 3H), 3.84 (s, 3H), 3.88 (s, 6H), 7.25 (s, 2H), 7.44 (d, 1H, J=0.6 Hz), 8.02 (d, 1H, J=1.2 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
PREPARATION EXAMPLE 19 Synthesis of Ethyl 6-(3,4,5-trimethoxyphenyl)picolinate 3,4,5-Trimethoxyphenylboronic acid (837 mg) and <strong>[21190-89-6]ethyl 6-chloropicolinate</strong> (733 mg) were reacted in the same manner as in Preparation Example 1 to obtain the title compound. Yield: 929 mg (74%). 1H-NMR (400 MHz, CDCl3) delta: 1.46 (t, 3H, J=7.1 Hz), 3.90 (s, 3H), 3.98 (s, 6H), 4.49 (q, 2H, J=7.1 Hz), 7.30 (s, 2H), 7.84-7.94 (m, 2H), 8.03(dd, 1H, J=7.2 Hz, 1.5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
PREPARATION EXAMPLE 23 Synthesis of 4-(3,4,5-Trimethoxyphenyl)pyridine-N-oxide 3,4,5-Trimethoxyphenylboronic acid (2.49 g) and <strong>[14248-50-1]4-bromopyridine-N-oxide</strong> (2.25 g) were reacted in the same manner as in Preparation Example 1 to obtain the title compound. Yield: 2.69 g (88%). 1H-NMR (400 MHz, CDCl3) delta: 3.90 (s, 3H), 3.93 (s, 6H), 6.76 (s, 2H), 7.47 (d, 2H, J=7.1 Hz), 8.25 (d, 2H, J=7.1 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
PREPARATION EXAMPLE 54 Synthesis of 4-methyl-2-(3,4,5-Trimethoxyphenyl)-pyrimidine 2-Bromo-4-methylpyrimidine (1.5 g) and 3,4,5-trimethoxyphenylboronic acid (1.83 g) were reacted in the same manner as in Preparation Example 1 to obtain the title compound. Yield: 1.49 g (67%). 1H-NMR (400 MHz, CDCl3) delta: 2.57 (s, 3H), 3.92 (s, 3H), 3.99 (s, 6H), 7.01 (d, 1H, J=5.1 Hz), 7.77 (s, 2H), 8.61 (d, 1H, J=5.1 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
tris-(dibenzylideneacetone)dipalladium(0); | Example 150 4-(3,4-diethoxyphenyl)-4-oxo-N-[6-phenyl-4-(3,4,5-trimethoxyphenyl)pyridin-2-yl]butanamide Using N-(4-chloro-6-phenylpyridin-2-yl)-4-(3,4-diethoxyphenyl)-4-oxobutanamide obtained in Example 43-(3) (22.6 mg), tris(dibenzylideneacetone)dipalladium (1.1 mg), biphenyl-2-yl(dicyclohexyl)phosphine (1.8 mg), 1N aqueous potassium carbonate solution (0.1 mL) and (3,4,5-trimethoxyphenyl)boronic acid (26.5 mg) as starting materials and in the same manner as in Example 119, 4-(3,4-diethoxyphenyl)-4-oxo-N-[6-phenyl-4-(3,4,5-trimethoxyphenyl)pyridin-2-yl]butanamide (16.9 mg) was obtained. HPLC (220 nm) purity 100% (retention time 2.05 min) MS (ESI+, m/e) 585 (M+H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
tris-(dibenzylideneacetone)dipalladium(0); | Example 182 4-(2,3-dihydro-1-benzofuran-5-yl)-4-oxo-N-[6-phenyl-4-(3,4,5-trimethoxyphenyl)pyridin-2-yl]butanamide Using N-(4-chloro-6-phenylpyridin-2-yl)-4-(2,3-dihydro-1-benzofuran-5-yl)-4-oxobutanamide obtained in Example 114-(1) (20.3 mg), tris(dibenzylideneacetone)dipalladium (1.1 mg), biphenyl-2-yl(dicyclohexyl)phosphine (1.8 mg), 1N aqueous potassium carbonate solution (0.1 mL) and (3,4,5-trimethoxyphenyl)boronic acid (26.5 mg) as starting materials and in the same manner as in Example 119, 4-(2,3-dihydro-1-benzofuran-5-yl)-4-oxo-N-[6-phenyl-4-(3,4,5-trimethoxyphenyl)pyridin-2-yl]butanamide (17.7 mg) was obtained. HPLC (220 nm) purity 93% (retention time 1.98 min) MS (ESI+, m/e) 539 (M+H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With 1,2-bis(phenylsulfinyl)ethane palladium(II) acetate; acetic acid; p-benzoquinone In 1,4-dioxane at 45℃; for 4h; optical yield given as %de; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 100℃; for 19h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 52 %Spectr. 2: 3.5 %Spectr. 3: 2.5 %Spectr. | With tetrakis(triphenylphosphine) palladium(0); potassium chloride; sodium carbonate In ethanol; water; toluene at 100℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; ethanol; water Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In acetonitrile; at 150℃; for 0.166667h;Microwave reactor; | A mixture of 5-bromo-l,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (200mg, 0.939 mmol), 3,4,5-trimethoxyphenylboronic acid (239 mg, 1.127 mmol) and dichlorobis(triphenylphosphine)palladium (II) (33 mg, 0.047 mmol) in CH3CN (5 ml) and 1 M Na2CO3 (5 ml) was heated in a microwave reactor for 10 min at 1500C. The reaction mixture was filtered, evaporated, partitioned between water and DCM and purified by silica gel chromatography with 0-10% MeOH:DCM to obtain 85 mg (30%) of compound No.. 1H NMR (CDCl3/DMSO-d6, 300 MHz): delta 10.19 (bs, IH), 8.18 (d, J = 1.1 Hz, IH), 7.54 (s, IH), 6.57 (s, 2H), 3.80 (s, 6H), 3.75 (s, 3H), 3.47 (s, 2H). |
30% | With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In acetonitrile; at 150℃; for 0.166667h;Microwave irradiation; | Preparation of 5-(3,4,5-trimethoxy-phenyl)-l,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (Intermediate BY)[0353] A mixture of 5-bromo-l,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (200mg, 0.939 mmol), 3,4,5-trimethoxyphenylboronic acid (239 mg, 1.127 mmol) anddichlorobis(triphenylphosphine)palladium (II) (33 mg, 0.047 mmol) in CH3CN (5 ml) and 1 MNa2CC"3 (5 ml) was heated in a microwave reactor for 10 min at 150C. The reaction mixture was filtered, evaporated, partitioned between water and DCM and purified by silica gel chromatography with 0-10% MeOH:DCM to obtain 85 mg (30%) of compound No.. 1H NMR (CDCl3/DMSO-d6, 300 MHz): delta 10.19 (bs, 1H), 8.18 (d, J= 1.1 Hz, 1H), 7.54 (s, 1H), 6.57 (s, 2H), 3.80 (s, 6H), 3.75 (s, 3H), 3.47 (s, 2H). |
30% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In acetonitrile; at 150℃; for 0.166667h;Microwave irradiation; | In reference to Scheme 15, a mixture of 5-bromo-l,3-dihydro-pyrrolo[2,3- b]pyridin-2-one (200mg, 0.939 mmol), 3,4,5-trimethoxyphenylboronic acid (239 mg, 1.127 mmol) and dichlorobis(triphenylphosphine)palladium (II) (33 mg, 0.047 mmol) in CH3CN (5 ml) and 1 M a2CC>3 (5 ml) was heated in a microwave reactor for 10 min at 150C. The reaction mixture was filtered, evaporated, partitioned between water and DCM and purified by silica gel chromatography with 0-10% MeOH:DCM to obtain 85 mg (30%) of Intermediate A. NMR (CDCl3/DMSO-d6, 300 MHz): delta 10.19 (bs, 1H), 8.18 (d, J= 1.1 Hz, 1H), 7.54 (s, 1H), 6.57 (s, 2H), 3.80 (s, 6H), 3.75 (s, 3H), 3.47 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With 2-[2-(diisobutylphosphinyl)ethyl]pyridine; palladium diacetate; caesium carbonate In toluene at 110℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In methanol; water; toluene;Inert atmosphere; Reflux; | General procedure: To a solution of bromobiphenylaldehyde (6, 260 mg, 1 mmol) and various phenyl boronic acids (7a-j, 1 mmol) in 2 M aqueous sodium carbonate (2 mL) and toluene/ethanol (9:3 mL) is added a catalytic amount (0.4% mol) of tetrakis-triphenylphosphine palladium, and the mixture was reflux under argon atmosphere for 2-3 h. After completion of reaction, the suspension is cooled and extracted with ethyl acetate (3 × 30 mL) and the organic phase was washed with water and brine, dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to get the crude product. This residue was further purified by column chromatography using ethyl acetate and hexane to afford the pure terphenylaldehydes (8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water at 150℃; for 0.25h; Inert atmosphere; Microwave irradiation; | 39 3-(3,4,5-trimethoxyphenyl)-1H-indazole-5-carbaldehyde 3-iodo-5-formylindazole (210 mg, 0.735 mmol), trimethoxyphenyl boronic acid (187 mg, 0.882 mmol) and K2CO3 (309 mg, 2.21 mmol) were combined in 5:1 Dioxane:H2O (2 mL) and degassed with bubbling argon for 20 minutes. Pd(PPh3)4 (123 mg, 0.106 mmol) was added, and the reaction vessel purged with argon. The reaction was microwaved at 150° C. for fifteen minutes. The crude reaction mixture was diluted with EtOAc (20 mL), washed with 1M HCl (10 mL), H2O (10 mL) and brine (10 mL), dried with Na2SO4, and concentrated. The residue was purified on silica, eluting with 3:2 Hex:EtOAc, and the impure fractions containing product were concentrated to a yellow solid. This yellow solid was suspended in EtOAc and the white solids filtered to afford 140 mg (83%) of 3-(3,4,5-trimethoxyphenyl)-1H-indazole-5-carbaldehyde as a white solid. |
55% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 150℃; for 0.5h; Inert atmosphere; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 0.5 h / 150 °C / Inert atmosphere; Microwave irradiation 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h | ||
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water / 0.25 h / 150 °C / Inert atmosphere; Microwave irradiation 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With tert.-butylhydroperoxide; copper(l) iodide; In N,N-dimethyl acetamide; water; at 130℃; for 20h; | General procedure: Boronic acid 1 (0.5mmol), benzyl cyanide 2 (0.75mmol), CuI (95mg, 0.5mmol), tert-BuOOH (70% aq, 144muL, 1mmol), and DMAc (2mL) were placed in a 25mL round flask. The reaction mixture was stirred at 130C (oil bath) for 20h under air. After cooling to the room temperature, the resulting mixture was poured to 15mL water and extracted with dichloromethane (3×5mL). The organic phase was combined and dried over anhydrous Na2SO4. Dichloromethane was evaporated under reduced pressure and the residue was purified by flash column chromatography on a silica gel to give the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 90℃; for 0.0833333h;Microwave irradiation; Inert atmosphere; | General procedure: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmol%, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 C for 5-12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube; | ||
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With pyridine; pyridine N-oxide; copper diacetate; In dichloromethane; at 20℃;Molecular sieve; | A mixture of <strong>[27992-32-1]6-bromopyridin-2(1H)-one</strong> (3) (8.3g, 47.7mmol), (3,4,5-trimethoxyphenyl)boronic acid (20.1g, 94.8mmol), Cu(OAc)2 (0.9g, 5.0mmol), pyridine (7.7mL, 94.8mmol), pyridine-N-oxide (5.0g, 52.6mmol), 4AMS (2.0g) in dry CH2Cl2 (100mL) was stirred at room temperature overnight. Then CH2Cl2 (300mL) and NH3.H2O (50mL) were added, and the reaction mixture was filtered through Celite. The filtrate was washed with water, dried over Na2SO4, and evaporated to dryness to yield the crude product, which was triturated with CH2Cl2 (50mL) to give compound 4 as a white solid (13.0g, 77% yield). M.p.: 174.9-176.8C; 1H NMR (400MHz, CDCl3) delta 7.51 (t, J=7.8Hz, 1H), 7.20 (d, J=7.5Hz, 1H), 6.74 (d, J=8.1Hz, 1H), 6.40 (s, 2H), 3.84 (s, 3H), 3.82 (s, 6H); 13C NMR (100MHz, CDCl3) delta 163.12, 153.79, 149.69, 141.25, 139.32, 135.28, 122.44, 109.15, 98.56, 98.50, 61.00, 56.18. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In N,N-dimethyl-formamide; for 15h;Inert atmosphere; Reflux; | The mixture of compound 3 (10g, 57.5mmol), Pd(PPh3)4 (100mg, 0.09mmol), K2CO3 (18.2g, 0.132mol) and 3,4,5-trimethoxyphenylboronic acid (14.6g, 68.9mmol) in DMF (50mL) was refluxed under N2 (g) for 15h. After cooled to room temperature, the mixture was quenched with water (250mL), extracted with CH2Cl2 (100×3mL), and evaporated to dryness to give a crude product, which was purified by column chromatography to give 5 as a white solid (11.5g, 76% yield). M.p.: 194.8-196.1C; 1H NMR (400MHz, CDCl3) delta 12.26 (br, 1H), 7.49 (m, 1H), 6.99 (s, 2H), 6.48 (m, 2H), 3.98 (s, 6H), 3.91 (s, 3H); 13C NMR (100MHz, CDCl3) delta 165.14, 153.70, 146.95, 141.51, 139.63, 128.86, 118.17, 104.53, 103.98, 60.98, 56.34. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; N,N-dimethyl-formamide; acetonitrile; at 90℃; for 8h;Sealed tube; Inert atmosphere; | Synthesis of 2-amino-5-bromo-3-3,4,S-trimethoxyphenvl)pyridine (2). A mixture of 5- brotno-3-jodopyndin-2-amme (386 mg, 1 .30 mmolj. 3,4.5-trimethoxyphenviboronic acid (275 mg 1 0 mmol) and Pd( PPII ) (180 ing 0 1 6 nimol) ere added to a sealed tubeThe tube was evacuated and backfilled with argon (3 cycles). Acetonitrile (6.0 mL) and1)M1 (2 5 ml. ) xseie added In syringe at tooni tempetature to1loed in (1 M) aqueous Na2CO3 (2.6 mL, 2.60 mmoi). After being stirred at 90 C for about 8 h, the reaction mixture was iltered and concentrated. ?I?he residue was purified, by flash column chromatography to give 2 as white solid (235 mg, 80%). 1KN?MR. (500 MHz, CDCI.3) d 8.11(d J-2H7 1K) 4S(d 1-25117 111) 662(s 211) 390(s 311) 38(s 611) MS (ESI): 339.0 [Mr. |
80% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; N,N-dimethyl-formamide; acetonitrile; at 90℃; for 8h;Inert atmosphere; | A mixture of 5-bromo-3-iodopyridin-2-amine (386 mg, 1.30 mmol), 3,4,5-trimethoxypenylboronic acid (275 mg. 130 mmol) and Pd(PPh3)4 (I SO mg, 0.156 mmol) were added to sealed tube. The tube was evacuated and back filled with argon (3 cycles). Acetonitrile (6.0 mL) and DMF (2,5 ml.) were added by syringe at room temperature, followed by (1M) aqueous Na2CO3( (2.6 mL, 2.60 mmol). After being stirred at 90 C for about 8 h, the reaction mixture was filtered and concentrated. The residue was purified by flash column chromatography to give 2 as white solid (235 mg, 80%). 1HNMR (500 MHz, CDCb) 3 8.1 1 (d, J - 2.5 Hz, I E), 7.48 (d, J = 2.5 Hz, 1 H), 6.62 (s, 2H), 3.90 (s, 3H), 3.88 (s, 6H); MS (ESI): 339.0 [Mf. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With 5,5'-dimethyl-2,2'-bipyridine; methanesulfonic acid; palladium(II) trifluoroacetate; water In 2-methyltetrahydrofuran at 80℃; for 36h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.7% | With 5,5'-dimethyl-2,2'-bipyridine; methanesulfonic acid; palladium(II) trifluoroacetate; In 2-methyltetrahydrofuran; water; at 100℃; for 30h; | At room temperature,To the reaction vessel, 100 ml of a solvent (a mixture of 2-MeTHF and water in a volume ratio of 2: 1)20 mmol <strong>[96631-87-7]7-cyanoindole</strong>,60 mmol of 3,4,5-trimethoxybenzeneboronic acid,1.5 mmol palladium trifluoroacetate,2 mmol of the above ligand L2And 300 mmol methanesulfonic acid;With stirring, the temperature was raised to 100 C,And incubated for 30 hours.After the reaction was over, 100 ml of water was added to the reaction mixture and the mixture was extracted with ether 2-4 times. The combined ether layers were dried over anhydrous sodium sulfate, filtered and evaporated to remove the ether. The concentrate was passed through a 300-400 mesh silica gel column , A mixture of ethyl acetate / petroleum ether as eluent, ethyl acetate and petroleum ether volume ratio of 1:15, the concentration of the eluate,The title compound was obtained as a yellow solid, designated C. The yield was 75.7% with a purity of 98.9% (HPLC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.0 g | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 12h; | [13011 6-Bromo-3 -(3,4,5 -trimethoxyphenyl)imidazo [1 ,2-a]pyridine can be prepared asshown in Scheme 44: A reaction flask was charged with <strong>[474706-74-6]6-bromo-3-iodoimidazo[1,2-a]pyridine</strong> (2.0 g, 6.2 mmol), (3,4,5-trimethoxyphenyl)boronic acid (1.44 g, 6.8 mmol), 2M. aq. Na2CO3 (8 mL, 16 mmol), 1 ,4-dioxane (50 mL) and a stir bar. The contents were degassed by vacuum and back filled with argon in three times while stirring. Subsequently, catalyst Pd(PPh3)4 (0.35 g, 0.30 mmol) was added to the reaction contents, repeated degassing cycles and heated at 90 C for 12h. Reaction mixture was cooled and filtered the biphasic reaction mixture through Celite and concentrated the filtrate. The crude solid residue was partitioned between CH2C12(150 mL)/water (50 mL). The organic layer was separated, dried over Mg504, filtered and concentrated. The crude concentrate (2.2 g) was subjected to purification by flash column chromatography (Combiflash companion system with RediSep silica gel column 40 g, 30-60% EtOAC/hexanes as an eluting solvent) to obtain 6-bromo-3 -(3,4,5 -trimethoxyphenyl)imidazo [1 ,2-a]pyridine as a white solid(1.0 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; lithium chloride In 1,2-dimethoxyethane; water Reflux; | As shown with reference to Scheme 5 in Figure 5, as before, Suzuki-Miyaura coupling of 3,4,5-trimethoxyphenylbroronicacid with the appropriate 2-bromobenzaldehyde gave the biaryls (1). These in turn underwent vinyl Grignardreagent addition to the aldehyde function (giving compound 2) of Figure 5, and oxidation to give ketones 3. Five newexamples are summarized in the table below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; lithium chloride In 1,2-dimethoxyethane; water Reflux; | As shown with reference to Scheme 5 in Figure 5, as before, Suzuki-Miyaura coupling of 3,4,5-trimethoxyphenylbroronicacid with the appropriate 2-bromobenzaldehyde gave the biaryls (1). These in turn underwent vinyl Grignardreagent addition to the aldehyde function (giving compound 2) of Figure 5, and oxidation to give ketones 3. Five newexamples are summarized in the table below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; lithium chloride; In 1,2-dimethoxyethane; water;Reflux; | As shown with reference to Scheme 5 in Figure 5, as before, Suzuki-Miyaura coupling of 3,4,5-trimethoxyphenylbroronicacid with the appropriate 2-bromobenzaldehyde gave the biaryls (1). These in turn underwent vinyl Grignardreagent addition to the aldehyde function (giving compound 2) of Figure 5, and oxidation to give ketones 3. Five newexamples are summarized in the table below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; lithium chloride; In 1,2-dimethoxyethane; water;Reflux; | As shown with reference to Scheme 5 in Figure 5, as before, Suzuki-Miyaura coupling of 3,4,5-trimethoxyphenylbroronicacid with the appropriate 2-bromobenzaldehyde gave the biaryls (1). These in turn underwent vinyl Grignardreagent addition to the aldehyde function (giving compound 2) of Figure 5, and oxidation to give ketones 3. Five newexamples are summarized in the table below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2H,3H,4H-pyrido[1,2-a]pyrimidine-2,4-dione With potassium carbonate; p-toluenesulfonyl chloride In 1,4-dioxane; water at 25 - 28℃; for 1h; Stage #2: 3,4,5-trimethoxyphenylboronic Acid With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; | 4.1.2 Typical experimental procedure for the synthesis of 2-aryl-4H-pyrido[1,2- a]pyrimidin-4-ones (3a-r): [21] General procedure: A mixture of the 4H-pyrido[1,2-a]pyrimidin-4-one (1mmol), and K2CO3 (2.5eq) in 1,4-dioxane (2mL) and H2O (1mL) taken in a round-bottomed flask and p-TsCl (1.3eq) was added to it. The mixture was stirred under open air for 1h at rt (25-28°C). The boronic acid (1.2eq) and Pd(PPh3)4 (3mol %) were subsequently added and the mixture was heated at 100°C under open air. Upon completion of reaction as indicated by TLC (1-1.5h), the resultant mixture was cooled to rt and extracted with EtOAc (2×25mL). The combined organic solution was washed with water (2×5mL) and brine (1×5mL), dried with anhyd. Na2SO4, and concentrated under reduced pressure. The column chromatographic purification of crude mass was performed on neutral alumina using EtOAc-hexane (30-40%) as eluting solvent afford the arylated products (3a-r). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium permanganate In acetonitrile at 90℃; for 1h; Schlenk technique; regioselective reaction; | General procedure for synthesis of 2-arylquinoline N-oxide derivatives 3a-u General procedure: In a 50mL Schlenk tube, quinoline N-oxides 1 (0.3mmol), arylboronic acids 2 (0.6mmol), and KMnO4 (0.6 mmol, 94.8 mg) in acetonitrile (3.0 mL) were added and the reaction was continued at 90 °C for 1.0 h (monitored by TLC). The reaction mixture was diluted with ethyl acetate, then washed with saturated sodium chloride solution for three times. The resulting organic phase was dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography using ethyl acetate/petroleum ether (1:3 to 2:1) as eluant to obtain the desired products 3a-u. All compounds were confirmed by IR, 1H NMR, 13C NMR, and MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: 2-phenyl-4(3H)-quinazolinone With sodium ethanolate; p-toluenesulfonyl chloride In 1,4-dioxane at 70℃; for 0.333333h; Stage #2: 3,4,5-trimethoxyphenylboronic Acid With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); water In 1,4-dioxane | Synthesis of 2,4-disubstituted quinazolines (3a-3n): General procedure: The solution of quinazolin-4-ones (1 eq) in 1,4-dioxane (3 mL)was treated with tosyl chloride (1.1 eq) and NaOEt (2.0 eq) at70 °C. After 20 min, boronic acid (1.25 equiv), Pd(PPh3)4 (0.05eq), CuI (0.05 eq) and H2O (0.5 mL) were added under air atmosphere. After the completion of the reaction as indicated by TLC, the solvent was evaporated and the residue was purified on silica gel to provide the products 3a-3n (Fig. 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With pyridine; copper diacetate; In dichloromethane; | To a solution of <strong>[24807-55-4]3-nitro-1H-1,2,4-triazole</strong> (500 mg, 4.38 mmol; CAS: 24807-55-4) in DCM (50 mL) was added copper (II) acetate (1194 mg, 6.58 mmol), 3,4,5-trimethoxyphenylboronic acid (415a) (1859 mg, 8.77 mmol; CAS: 182163-96-8) and pyridine (0.71 mL, 8.77 mmol). The resulting mixture was stirred overnight under air atmosphere and concentrated in vacuum to dryness. The residue was taken up with EtOAc and filtered through a Celite pad, the filtrate was concentrated in vacuum and the obtained residue was purified by flash column chromatography [silica (12 g), eluting with EtOAc in hexane from 0-50%] to furnish 3-nitro- 1- (3,4,5-trimethoxyphenyl)-lH-l,2,4-triazole (415b) (560 mg, 46% yield) as a white solid; MS (ES+): 281.1 (M+l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In N,N-dimethyl-formamide; for 10h;Autoclave; Reflux; | In a 20 liter autoclave, 1264 g (2 mol) of tetrabromospiro and 1865 g (8.8 mol) of 3,4,5-trimethoxyphenylboronic acid were added, and 6 liters of an aqueous solution containing sodium hydroxide (352 g, 8.8 mol) was further added. And 4 liters of DMF, a coupling reaction catalyst tetrakis(triphenylphosphine)palladium 69 g (0.06 mol) was added in one portion, and the reaction liquid was heated under reflux for 10 hours. The heating was stopped, 2.5 liters of water was added to the reaction system, and the reaction liquid was cooled to room temperature to precipitate a large amount of granular white solid. The liquid (DMF and water mixture) was slowly discharged from the bottom of the reaction vessel, and the solid was left in the kettle until the liquid was completely discharged. 4 liters of ethyl acetate was added to the reaction vessel to dissolve the solid. The organic layer was extracted with water to neutrality, washed with saturated brine, and the aqueous layer was separated and extracted.The type of desiccant is immersed and dried for 30 minutes, the desiccant is taken out, and the mixture is distilled in a kettle to remove the solvent to obtain a viscous coupling product, which is directly used for the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.9% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 12h; Inert atmosphere; | 4.1 Take (1.0g, 5.08mmol) 5-bromoindazole in 27mL of dioxane and 3mL of water.To the solution was added (1.18 g, 5.58 mmol) 3,4,5-trimethoxyphenylboronic acid, (1.08 g, 10.15 mmol) sodium carbonate, (100 mg) 1,1'-bis (di-tert-butylphosphino) ) Ferrocene palladium dichloride, protected by nitrogen, and reacted at 80 ° C. for 12 h.The reaction was monitored by TLC. After the reaction was completed, the reaction solution was concentrated, and the concentrate was extracted with ethyl acetate-water.The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated.995 mg of solid was obtained by petroleum ether-ethyl acetate 4: 1 column chromatography with a yield of 68.9%. |
68.9% | With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium carbonate In 1,4-dioxane; water at 80℃; for 4h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 95℃;Inert atmosphere; | General procedure: Generalprocedure. A solution of 6-chloro-2-cyano-3-nitropyridine (1 equiv) in toluene or dioxane/water (see compound description) was degassed with argon and subsequently, the corresponding aryl boronic acid (1.2equiv), Pd(PPh3)4 (0.02 equiv) and K2CO3 (2 equiv) were added. The mixture was degassed a second time, filled with argon and stirred at 95 C overnight. After completion of the reaction as monitored by TLC,the volatiles were evaporated to dryness and the crude residue was diluted with EtOAc (20 mL) and washed with water (2×20 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated invacuo. The resulting residue was purified by silica gel flash chromatography, yielding the corresponding 6-aryl-3-nitropyridine-2-carbonitrile. The following compounds were made according to this procedure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With rongalite In ethanol; water at 20℃; for 8h; Irradiation; | General Procedure General procedure: To a clean and dry round bottom flask, phenylboronic acid (76 mg, 0.5 mmol), sodium hydroxymethane sulfinate dihydrate (Rongalite) (1.0 mmol) and 1 mL of EtOH:H2O (3:1) solvent mixture were added. The resulting mixture was stirred at room temperature under sunlight irradiation in open to air for completion. The reaction progress was monitored by TLC. After reaction completion, solvent mixture was evaporated under vacuum, the crude product was extracted with ethyl acetate (3 x 10 mL). The combined organic layers were dried on anhydrous Na2SO4, solvent was evaporated under vacuum. The residue was purified by using silica gel as a stationary phase and ethyl acetate/hexanes as an eluent. All reactions kept under direct sunlight between 11 am and 4 pm and the average solar intensity was 500-600 W/m2, which was measured with Newport Optical Power meter/Energy meter (Model 842.PE). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere; Schlenk technique; | 4.2 General procedure for the synthesis of ketones (3a-r) General procedure: Under a nitrogen atmosphere, aryl acetonitrile 1 (3mmol), arylboronic acids 2 (6mmol), palladium acetate (5mol %), 2,2′-Bipyridine (10mol %), trifluoroacetic acid (30mmol), potassium fluoride (6mmol), tetrahydrofuran (20mL), and water (10mL) were successively added to a Schlenk reaction tube. The reaction mixture was stirred vigorously at 80°C for 2h. After the reaction mixture was cooled to room temperature, saturated sodium bicarbonate (30mL) was added into the solution, and the mixture was extracted with ethyl acetate (10mL) for 3 times. The combined organic layer was concentrated in vacuo. The residue was purified by flash column chromatography to afford desired product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid; In tetrahydrofuran; water; at 80℃; for 2.0h;Inert atmosphere; Schlenk technique; | General procedure: Under a nitrogen atmosphere, aryl acetonitrile 1 (3mmol), arylboronic acids 2 (6mmol), palladium acetate (5mol %), 2,2′-Bipyridine (10mol %), trifluoroacetic acid (30mmol), potassium fluoride (6mmol), tetrahydrofuran (20mL), and water (10mL) were successively added to a Schlenk reaction tube. The reaction mixture was stirred vigorously at 80C for 2h. After the reaction mixture was cooled to room temperature, saturated sodium bicarbonate (30mL) was added into the solution, and the mixture was extracted with ethyl acetate (10mL) for 3 times. The combined organic layer was concentrated in vacuo. The residue was purified by flash column chromatography to afford desired product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere; Schlenk technique; | 4.2 General procedure for the synthesis of ketones (3a-r) General procedure: Under a nitrogen atmosphere, aryl acetonitrile 1 (3mmol), arylboronic acids 2 (6mmol), palladium acetate (5mol %), 2,2′-Bipyridine (10mol %), trifluoroacetic acid (30mmol), potassium fluoride (6mmol), tetrahydrofuran (20mL), and water (10mL) were successively added to a Schlenk reaction tube. The reaction mixture was stirred vigorously at 80°C for 2h. After the reaction mixture was cooled to room temperature, saturated sodium bicarbonate (30mL) was added into the solution, and the mixture was extracted with ethyl acetate (10mL) for 3 times. The combined organic layer was concentrated in vacuo. The residue was purified by flash column chromatography to afford desired product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; | 4.1.2. General procedures for the synthesis oftrimethoxyphenylbenzo[d]oxazoles 4a-u and 5a-h General procedure: To a mixture of bromobenzo[d]oxazoles (1 mmol) and K2CO3(1.09 mmol, 0.15 g) in mixed solvent (DMF: EtOH: H2O 7:2:1,5 mL), a solution of Pd(PPh3)4 (0.04 mmol, 0.046 g) in mixed solvent(DMF: EtOH: H2O 7:2:1, 0.5 mL) was added under Ar at 80 °C.Then, the reaction mixture was stirred at 80 °C for 10 h. After the reaction was completed, the reaction mixture was cool to roomtemperature, and dumped into the water (50 mL), and extractedwith ethyl acetate (3x15 mL). The organic layer was dried bysodium sulfate and concentrated in a vacuum to provide a crude.The obtained crude was purified by chromatography (n-hexane:ethyl acetate 10:1, vv) to yield the corresponding trimethoxyphenylbenzo[d]oxazoles. 2-Phenyl-7-(3,4,5-trimethoxyphenyl)benzo[d]oxazole (4a).White solid (isolated yield 79%). M. p.: 154.4-155.6 °C. 1H NMR(400 MHz, CDCl3) δ 8.27-8.25 (m, 2H), 7.75 (d, J = 7.8 Hz, 1H),7.55-7.52 (m, 4H), 7.43 (t, J 7.8 Hz, 1H), 7.15 (s, 2H), 3.99 (s, 6H),3.96 (s, 3H). 13C NMR (101 MHz, CDCl3) d 163.10, 153.51, 148.07, 142.81, 138.18, 131.66, 131.17, 129.01, 127.53, 127.09, 125.08, 123.96,118.97, 105.58, 61.00, 56.28. HR-MS (ESI) calcd for C22H20NO4 [M H]: 362.1387, found: 362.1398. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46.7% | With pyridine; copper diacetate In dichloromethane at 20℃; | 6.1.2. General procedures of compounds 2a-e General procedure: To a solution of 5-aminoquinoline (1) (100 mg, 0.694 μmol) in 5 mLdichloromethane was added arylboronic acid (0.832 mmol), pyridine(2.08 mmol, 3.0 equiv) and Cu(OAc)2 (0.139 mmol, 0.2 equiv). Themixture was stirred at room temperature for overnight. Then the solventwas removed in vacuo. After that the residue was diluted by water, andextracted with ethyl acetate. The combined organic layer was thenwashed with brine, dried over anhydrous Na2SO4 and concentrated invacuo to provide the crude product, which was subjected to silica gelcolumn chromatography eluted with petroleum and ethyl acetate to givecompounds 2a-e. 6.1.3. N-(3,4,5-trimethoxyphenyl)quinolin-5-amine (2a) C18H18N2O3Yellow solid; yield: 46.7%. 1H NMR (400 MHz, CDCl3) δ 8.95-8.90(m, 1H), 8.37 (d, J = 8.5 Hz, 1H), 7.80 (d, J = 8.4 Hz, 1H), 7.61 (t, J =8.0 Hz, 1H), 7.35 (dd, J = 13.8, 6.1 Hz, 2H), 6.24 (s, 2H), 3.82 (s, 3H),3.75 (s, 6H). 13C NMR (101 MHz, CDCl3) δ 116.48, 112.97, 111.76,102.92, 102.07, 93.40, 93.11, 92.26, 86.26, 85.01, 82.82, 78.10, 58.60,23.57, 18.57. ESI-MS m/z 311.13 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; water monomer; toluene at 70℃; for 5h; Inert atmosphere; | 4.1.1. The synthesis of intermediate 8 4-Chloro-5-bromo-pyrimidine (7, 5.00 g, 25.8 mmol), (3,4,5-trimethoxyphenyl) boric acid (6.30 g, 14.9 mmol) and potassiumcarbonate (7.14 g, 51.6 mmol) were dissolved in 75 mL of mixedsolvents (Toluene: Ethanol: Water 3 : 1: 1), then tetrakis(-triphenylphosphine)palladium (3.00 g, 2.58 mmol) was addedquickly. The flask was evacuated and backfilled with nitrogen forthree times. The resulting mixture was stirred at 70 C for 5 h andfollowed by TLC until completion. The mixture was filtered, and thefiltrate was collected and concentrated. The crude residue waspurified by silica gel chromatography to provide the title product 8.5-bromo-4-(3,4,5-trimethoxyphenyl)pyrimidine (8). White solid,yield 36%, m.p. 121.5e123.6 C. 1H NMR (400 MHz, DMSO-d6) d 9.22(s, 1H), 9.12 (s, 1H), 7.13 (s, 2H), 3.85 (s, 6H), 3.76 (s, 3H). 13C NMR(100 MHz, CDCl3) d 163.7, 160.4, 156.8, 153.0, 140.1, 131.8, 118.8,107.1, 60.9, 56.3. ESI-MS: m/z 325.0, 327.0 [MH]. C13H13BrN2O3(324.0, 326.0). |
36% | With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; water monomer; toluene at 70℃; for 5h; Inert atmosphere; | 4.1.1. The synthesis of intermediate 8 4-Chloro-5-bromo-pyrimidine (7, 5.00 g, 25.8 mmol), (3,4,5-trimethoxyphenyl) boric acid (6.30 g, 14.9 mmol) and potassiumcarbonate (7.14 g, 51.6 mmol) were dissolved in 75 mL of mixedsolvents (Toluene: Ethanol: Water 3 : 1: 1), then tetrakis(-triphenylphosphine)palladium (3.00 g, 2.58 mmol) was addedquickly. The flask was evacuated and backfilled with nitrogen forthree times. The resulting mixture was stirred at 70 C for 5 h andfollowed by TLC until completion. The mixture was filtered, and thefiltrate was collected and concentrated. The crude residue waspurified by silica gel chromatography to provide the title product 8.5-bromo-4-(3,4,5-trimethoxyphenyl)pyrimidine (8). White solid,yield 36%, m.p. 121.5e123.6 C. 1H NMR (400 MHz, DMSO-d6) d 9.22(s, 1H), 9.12 (s, 1H), 7.13 (s, 2H), 3.85 (s, 6H), 3.76 (s, 3H). 13C NMR(100 MHz, CDCl3) d 163.7, 160.4, 156.8, 153.0, 140.1, 131.8, 118.8,107.1, 60.9, 56.3. ESI-MS: m/z 325.0, 327.0 [MH]. C13H13BrN2O3(324.0, 326.0). |
Tags: 182163-96-8 synthesis path| 182163-96-8 SDS| 182163-96-8 COA| 182163-96-8 purity| 182163-96-8 application| 182163-96-8 NMR| 182163-96-8 COA| 182163-96-8 structure
[ 122775-35-3 ]
3,4-Dimethoxyphenylboronic acid
Similarity: 0.97
[ 182344-21-4 ]
(4-Hydroxy-3-methoxyphenyl)boronic acid
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[ 622864-48-6 ]
(3-Hydroxy-4-methoxyphenyl)boronic acid
Similarity: 0.97
[ 622864-48-6 ]
(3-Hydroxy-4-methoxyphenyl)boronic acid
Similarity: 0.97
[ 622864-48-6 ]
(3-Hydroxy-4-methoxyphenyl)boronic acid
Similarity: 0.97
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P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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