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CAS No. : | 380430-68-2 | MDL No. : | MFCD03411945 |
Formula : | C11H16BNO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CWLNHPXWZRALFS-UHFFFAOYSA-N |
M.W : | 237.06 | Pubchem ID : | 2773228 |
Synonyms : |
(3-Boc-Aminophenyl)boronic acid
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 66.51 |
TPSA : | 78.79 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) : | -6.76 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.39 |
Log Po/w (WLOGP) : | 0.52 |
Log Po/w (MLOGP) : | 0.69 |
Log Po/w (SILICOS-IT) : | -0.86 |
Consensus Log Po/w : | 0.35 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.12 |
Solubility : | 1.81 mg/ml ; 0.00764 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.65 |
Solubility : | 0.533 mg/ml ; 0.00225 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.25 |
Solubility : | 1.34 mg/ml ; 0.00566 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.55 |
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 |
---|---|---|
95% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; acetonitrile; at 130℃; for 0.166667h;Microwave radiation; | To a mixture of 7-chloro-4-((S)-3-methyl-morpholin-4-yl)-2-((S)-3-methyl-morpholin-4-yl)- pyrido[2,3-d]pyrimidine (1 equiv), potassium carbonate (1.2 equiv), and 3-BOC- 25 aminophenylboronic acid (1.2 equiv) in acetonitrile/water (1:1) (0.08 M of chloro-substrate) was added tetrakis(triphenylphosphine) palladium0 (0.05 equiv). The reaction vessel was sealed and exposed to microwave radiation (130 0C, medium absorption setting) for 10 minutes under nitrogen atmosphere. Upon completion the samples were filtered through a <n="235"/>silica cartridge, washed with ethyl acetate and then concentrated in vacuo. The crude residue was used as such in the next reaction.{3-[2,4-Bis-((S)-3-methyl-morpholin-4-yl)-pyrido[2,3-d]pyrimidin-7-yl]-phenyl}-carbamic acid tert-butyl ester: (95 % yield, 100 % purity) m/z (LC-MS, ESP): 520.9 [M+H]+ R7T = 3.23 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
For compounds (8-13, 58, 59) the commercially available 4-aminophenylboronic acid, 3-aminomethylphenylboronic acid and 2-aminophenylboronic acid were BOC protected under standard conditions (See above compounds 2-6) and the appropriate boronic acid was used at the Suzuki coupling stage in the synthesis of compounds (2-6). The BOC group was removed with: 4 M HCl in dioxane at RT after hydrazone coupling |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.0% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 5 - 6h;Heating / reflux; | To a stirred solution of Example 33 (200 mg5 0.51 mmol) and 3-(tert- butoxylcarbonylaminophenylboronic acid (246 mg, 1.03 mmol) in THF/water (1:1, 20 mL) was added tetrakis(triphenylphosphine)palladium(0) (59 mg5 0.05 mmol) and potassium carbonate (214 mg, 1.55 mmol) and the resulting mixture was heated to reflux for 5-6h. The progress of the reaction was monitored by TLC and after completion the reaction was cooled to room temperature. The mixture was diluted with ethyl acetate (100 mL) and the two layers were separated. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated in vacuum. The residue was purified by column chromatography using silica gel to give methyl-2-{8-[3-(tert- butyloxycarbonylamino)phenyl]-l5354,5-tetrahydro-2H-pyrido[453-b]indol-2-yl}pyrimidine- 5-carboxylate (160 mg, 62.0%; m/e = 500 (M+l)To a stirred solution of methyl-2-{8-[3-(tert-butyloxycarbonylamino)phenyl]- 1 ,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (160 mg, 0.320 mmol) in dry DCM (10 mL)5 TFA (0.247 mL, 3.20 mmol) was added under nitrogen atmosphere at 0 C. The reaction was maintained at room temperature for Ih. The progress of the reaction was monitored by TLC and after the completion the volatiles were removed by evaporation. The crude was washed with hexane to give Example 85 (120 mg, 93.75%). 1HNMR (200 MHz, CD3OD) delta: 3.0 (t, 2H, CH2), 3.9 (s, 3H, OCH3), 4.42 (t5 2H5 CH2), 5.25 (s, 2H, CH2), 7.3-7.9 (m, 7H, Ar-H), 8.9 (s, 2H5 pyrimidine-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 24 - 48h; | Example 140; 2-tert-Butyl-5-chloro-isothiazolin-3-one-1,1-dioxide [(2.3 g, 10 mmol)-prepared following general procedure AB) was coupled with 3-boc-amino-phenylboronic acid (3.0 g, 12 mmol) according to general procedure AC to give [3-(2-tert-butyl-1,1,3-trioxo-2,3-dihydro-1H-isothiazol-5-yl)-phenyl]-carbamic acid tert-butylester.; General Procedure AC: Pd(II)-Catalyzed Coupling Reactions; A solution of aryl boronic acid (1.0 eq) in anhydrous dioxane (0.1-0.5 M) was added potassium carbonate (5-10 eq), aryl halide (1.1 eq) and Pd Cl2 (dppf) (2.5 eq) under nitrogen atmosphere. The reaction mixture was degassed by the freeze-thaw method thrice and was heated at 80 C. for 24 to 48 hours. At completion the reaction mixture was cooled to 25 C., poured into water and extracted with dichloromethane. The combined organic layers were washed with brine, dried with MgSO4 and concentrated in vacuo. The crude residue was purified by flash chromatography to yield light red solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.5% | With sodium carbonate;1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; In tetrahydrofuran; at 60℃; for 6.5h;Inert atmosphere; | Example 1 Synthesis of t-butyl [3-(2-chloro-6,7-dimethoxyquinazolin-4-yl)phenyl]carbamate To a mixture of 1.00 g (3.86 mmol) of 2,4-dichloro-6,7-dimethoxyquinazoline, 1.14 g (4.63 mmol) of 3-(N-t-butoxycarbonylamino)phenyl borate, tetrahydrofuran (25 mL), and 2 M sodium carbonate aqueous solution (5 mL) were added palladium acetate (8.84 mg) and 1,1'-bis(diphenylphosphino)ferrocene (21.4 mg) in this order, and the mixture was stirred at 60C for 6.5 hours under a nitrogen atomosphere. The reaction mixture was allowed to cool, and ethyl acetate (25 mL) and 5% w/w sodium chloride solution (20 mL) were added to extract the organic layer. The organic layer was washed twice with 5% w/w sodium chloride solution (20 mL) and then concentrated under reduced pressure. To the concentration residue were added ethyl acetate (1 mL) and 2-propanol (4 mL), and the mixture was suspended by stirring at 40C for 0.5 hours. The suspension was cooled, and the precipitated crystals were collected by filtration and dried to give 1.48 g of a target product (yield: 91.5%). 1H-NMR (CDCl3) delta (ppm): 1.52 (9H, s), 3.97 (3H, s), 4.07 (3H, s), 6.62 (1H, br), 7.33 (1H, s), 7.38-7.43 (1H, m), 7.48-7.53 (3H, m), 8.00 (1H, br). ESI MS: m/z 438 (M+Na)+. |
91.5% | With sodium carbonate;1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; In tetrahydrofuran; water; at 60℃; for 6.5h;Inert atmosphere; | Production example 22 Synthesis of t-butyl [3-(2-chloro-6,7-dimethoxyquinazolin-4-yl)phenyl]carbamate To a mixture of 1.00 g (3.86 mmol) of 2,4-dichloro-6,7-dimethoxyquinazoline, 1.14 g (4.63 mmol) of 3-(N-t-butoxycarbonylamino)phenyl borate, tetrahydrofuran (25 mL), and 2 M sodium carbonate aqueous solution (5 mL) were added palladium acetate (8.84 mg) and 1,1'-bis(diphenylphosphino)ferrocene (21.4 mg) in this order, and the mixture was stirred at 60C for 6.5 hours under a nitrogen atmosphere. The reaction solution was allowed to cool, and ethyl acetate (25 mL) and 5% w/w sodium chloride solution (20 mL) were added to extract the organic layer. The organic layer was washed twice with 5% w/w sodium chloride solution (20 mL) and then concentrated under reduced pressure. To the concentration residue were added ethyl acetate (1 mL) and 2-propanol (4 mL), and the mixture was suspended by stirring at 40C for 0.5 hours. The suspension was cooled, and the precipitated crystals were collected by filtration and dried to give 1.48 g of a target product (yield: 91.5%, HPLC purity: 99.02%). 1H-NMP (CDCl3) delta (ppm): 1.52 (9H, s), 3.97 (3H, s), 4.07 (3H, s), 6.62 (1H, br), 7.33 (1H, s), 7.38-7.43 (1H, m), 7.48-7.53 (3H, m), 8.00 (1H, br). ESI MS: m/z 438 (M+Na)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; In propan-1-ol; for 1h;Reflux; | Intermediate [Example Int6.1tert-butyl [3-(2-amino[1 ,2,4]triazolo[1 ,5-a]pyridin-6-yl)phenyl]carbamateTo a stirred solution of Int1.2 (5.0 g) in 1 -propanol (350 ml) was added 2M potassium carbonate solution (34.5 ml), {3-[(tert-butoxycarbonyl) amino] phenyl} boronic acid (10.9 g), triphenylphosphine (126 mg) and PdCl2(PPh3)2 (1 .61 g). The mixture was heated to reflux for 1 h, the solvent was removed in vacuum, water was added and the mixture was extracted with ethyl acetate and methanol (9: 1 ). The organic phase was dried (sodium sulfate), filtered through Celite and the solvent was removed in vacuum. The residue was triturated with DCM to give the title compound as a white solid. Yield: 6.65 g. 1 H-NMR (300MHz, DMSO-d6): delta [ppm]= 1 .49 (s, 9H), 6.08 (s, 2H), 7.26 - 7.39 (m, 2H), 7.44 (dd, 2H), 7.65 (dd, 1 H), 7.78 (s, 1 H), 8.74 (d, 1 H), 9.45 (s, 1 H). | |
With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; In propan-1-ol; for 1h;Reflux; | Intermediate Example Int9.1tert-butyl [3-(2-amino[1 ,2,4]triazolo[1 ,5-a]pyridin-6-yl)phenyl]carbamateTo a stirred solution of Int1.2 (5.0 g) in 1 -propanol (350 ml) was added 2M potassium carbonate solution (34.5 ml), (3-[(tert-butoxycarbonyl) amino] phenyl} boronic acid (10.9 g), triphenylphosphine (126 mg) and PdCl2(PPh3)2 (1.61 g). The mixture was heated to reflux for 1h, the solvent was removed in vacuum, water was added and the mixture was extracted with ethyl acetate and methanol (9:1 ). The organic phase was dried (sodium sulfate), filtered through Celite and the solvent was removed in vacuum. The residue was titurated with DCM to give the title compound as a white solid. Yield: 6.65 g. 1H-NMR (300MHz, DMSO-d6): delta [ppm]= 1.49 (s, 9H), 6.08 (s, 2H), 7.26 - 7.39 (m, 2H), 7.44 (dd, 2H), 7.65 (dd, 1H), 7.78 (s, 1H), 8.74 (d, 1 H), 9.45 (s, 1 H). | |
With potassium carbonate; triphenylphosphine;bis-triphenylphosphine-palladium(II) chloride; In propan-1-ol; for 1h;Reflux; | To a stirred solution of Int1.2 (5.0 g) in 1-propanol (350 ml) was added 2M potassium carbonate solution (34.5 ml), {3-[(tert-butoxycarbonyl) amino] phenyl} boronic acid (10.9 g), triphenylphosphine (126 mg) and PdCl2(PPh3)2 (1.61 g). The mixture was heated to reflux for 1h, the solvent was removed in vacuum, water was added and the mixture was extracted with ethyl acetate and methanol (9:1). The organic phase was dried (sodium sulfate), filtered through Celite and the solvent was removed in vacuum. The residue was triturated with DCM to give the title compound as a white solid. Yield: 6.65 g. 1H-NMR (300MHz, DMSO-d6): delta [ppm]= 1.49 (s, 9H), 6.08 (s, 2H), 7.26 - 7.39 (m, 2H), 7.44 (dd, 2H), 7.65 (dd, 1 H), 7.78 (s, 1 H), 8.74 (d, 1 H), 9.45 (s, 1 H). |
With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; In propan-1-ol; water; for 1h;Reflux; | To a stirred solution of Int1.2 (5.0 g) in 1-propanol (350 ml) was added 2M potassium carbonate solution (34.5 ml), {3-[(tert-butoxycarbonyl) amino] phenyl} boronic acid (10.9 g), triphenylphosphine (126 mg) and PdCl2(PPh3)2 (1.61 g). The mixture was heated to reflux for 1 h, the solvent was removed in vacuum, water was added and the mixture was extracted with ethyl acetate and methanol (9:1). The organic phase was dried (sodium sulfate), filtered through Celite and the solvent was removed in vacuum. The residue was titurated with DCM to give the title compound as a white solid. Yield: 6.65 g. 1H-NMR (300MHz, DMSO-d6): delta [ppm]= 1.49 (s, 9H), 6.08 (s, 2H), 7.26 - 7.39 (m, 2H), 7.44 (dd, 2H), 7.65 (dd, 1 H), 7.78 (s, 1 H), 8.74 (d, 1 H), 9.45 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In isopropyl alcohol; toluene; at 130℃; for 1.5h;Inert atmosphere; Microwave irradiation; | General procedure: A microwave vial was charged with the arylbromide (12g or 23, 300 mg, 0.90 mmol), the boronic acid (ArB(OH)2, 1.80 mmol), toluene (3 mL), i-PrOH (0.8 mL), and a 2.0 M Na2CO3-solution (0.50 mL). This mixture was degassed for 15 min by bubbling N2 through the mixture using a needle. Next, Pd(PPh3)4 (52 mg, 0.045 mmol) was added to the mixture and the vial was immediately capped and again degassed for 5 min. The vial was heated in the microwave for 90 min at 130 C. After this, the reaction mixture was filtered over Celite and most of the organic solvents were evaporated in vacuo. The pH of the residue was adjusted to pH >11 with a 1.0 M aq NaOH solution and the mixture was extracted with DCM (3×). The combined DCM layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. This afforded the crude product, which was purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium acetate; sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In acetonitrile; at 130℃; for 0.666667h;Microwave irradiation; | Example 50 Tert-butyl 3-(4-amino-1-methyl-1H-pyrazol-5-yl)phenylcarbamate To a 10 mL microwave vial was added 5-chloro-1-methyl-4-nitro-1H-pyrazole (150 mg, 0.93 mmol), <strong>[380430-68-2]3-(tert-butoxycarbonylamino)phenylboronic acid</strong> (440 mg, 1.86 mmol), dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) (152 mg, 0.019 mmol), a 1:1 M solution of Na2CO3/KOAc (1 mL) and acetonitrile (4 mL). The mixture was irradiated to 130 C. with a microwave for 40 min and the mixture was cooled, concentrated and purified via flash chromatography, heptane/ethyl acetate 20% to 95% to afford a yellow oil. To a 50 mL round bottom flask was added the nitro compound (120 mg, 0.90 mmol), iron (156 mg, 2.8 mmol), ammonium chloride (200 mg, 3.7 mmol), ethanol (10 mL) and water (1.5 mL). The mixture was stirred for 1 h and the reaction was monitored by LCMS. Upon completion of the reaction, the mixture was filtered through a pad of Celite and was washed with ethyl acetate (30 mL) and a 10% aqueous solution of K3PO4 (30 mL). The organic layer was washed with water (30 mL), dried over Na2SO4 and the organic solvent was distilled off to yield tert-butyl 3-(4-amino-1-methyl-1H-pyrazol-5-yl)phenylcarbamate as a brown oil with a purity of >98% (120 mg, 45%) over two steps. ESIMS m/z=289.1 (M+1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine;copper diacetate; In dichloromethane; at 20℃;4 A Molecular sieve; | Step 1: methyl 7-{3-[(tert-butoxycarbonyl)amino]phenoxy}-1,2,3,4-tetrahydronaphthalene-2-carboxylate Intermediate 49To a mixture of methyl 7-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate (Int-1, 250 mg, 1.2 mmol) in methylene chloride (10 mL) and triethylamine (1 mL, 9 mmol) were added 3-(N-Boc-amino)phenylboronic acid (664 mg, 2.8 mmol), copper(II) acetate (0.509 g, 2.8 mmol) and 4 molecular sieves (approx. 200 mg). The mixture was stirred overnight at room temperature. The reaction mixture was then filtered through Celite and the filtrate concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (0-100% ethyl acetate in hexanes gradient) to provide the product as an impure oil (73 mg, 15%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | With potassium phosphate;chloro(di-2-norbornylphosphino)(2'-dimethylamino-1,1'-biphenyl-2-yl)palladium(II); In 1,4-dioxane; water; at 160℃; for 1.5h;Microwave irradiation; | Intermediate 59:1 ,1-dimethylethyl {3-[4-(4-morpholinylmethyl)-6-([1 ,3]thia2oio[5,4-i)]pyridin-2- ylamino)-2-pyrimidinylJphenyl}carbamateA microwave vial was charged with A/-[2-chloro-6-(4-morpholinyimethyl)-4- pyrimidinyl][1 ,3]thiazo.o[5,4-i)]pyndin-2-amine (200 mg, 0.551 mmol), [3-([(1 , 1- dimethylethyl)oxy]carbonyl}amino)pheny[jboronic acid (261 mg, 1.102 mmol), chioro[2'- (dimethylamino)-2-biphenylyl]pa.ladium - (1 R,4S)-bicydo[2.2.1 ]hept-2-yl[(1 S,4f?)- bicyclo[2.2.1]hept-2-yl]phosphane (1 : 1 ) (30.9 mg, 0.055 mmol) and tripotassium phosphate (468 mg, 2.205 mmo.) in 1 ,4-dioxane (4 ml) and water (1 ml). The vial was sealed and was heated in a Biotage Initiator microwave system at 160 C for 1.5 hours. After cooling, the reaction mixture was partitioned between dichioromethane and saturated aqueous sodium bicarbonate. The organic extract was dried using a hydrophobic frit and evaporated to dryness. The residue was subjected to purification by mass directed automated preparative HPLC (ammonium bicarbonate modifier) to afford the title compound (20 mg, 0.038 mmol, 7 % yield). LCMS (Method B): Rt 2.99 minutes; m/z 520 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In water; N,N-dimethyl-formamide; at 92℃; for 4h;Inert atmosphere; | Example 24 - 5-(3-Acetylamino-phenyl)-3-ri-ethyl-5-(4-methyl-cvclohexyl)-l,2,3,6- tetrahvdro-pyridin-4-vH -thiophene-2-carboxylic acid; [284] DMF (10 mL) and H20 (2 mL) were added to a mixture of [3-({ [(1,1- dimethylethyl)oxy]- carbonyl}amino)phenyl]boronic acid (0.33 g, 1.4 mmol), 014C (0.43 g, 0.91 mmol), Pd(dppf)Cl2 (0.033 g, 0.0455 mmol), and sodium carbonate (0.3 g, 2.8 mmol) under N2, and stirred at 92 C for 4 hr. The reaction was cooled to RT, and to it was added ice -water and EtOAc. The organic layer was washed with water (3x) and the combined aqueous layers were back-extracted with EtOAc (2x). The combined organic layers were washed with brine, dried over anhydrous Na2S04, and concentrated under reduced pressure. The product was purified by flash chromatography (silica gel), eluting with 0-5% MeOH in CH2 + = 539. MS found: (M+H)+ = 539. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); XPhos; In 1,4-dioxane; water; at 80℃; for 18h;Inert atmosphere; | A mixture of 1 ,4-dioxane and water (3:1 , 9.36 ml) was degassed by bubbling nitrogen gas through the mixture. Intermediate 62 (2.00 g, 3.12 mmol), [3-(tert- butoxycarbonylamino)phenyl]boronic acid (780 mg, 3.28 mmol), tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.06 mmol), 2-dicyclohexylphosphino-2',4',6'- triisopropylbiphenyl (Xphos) (1 19 mg, 0.25 mmol) and potassium phosphate tribasic (3.307 g, 5 eq.) were added and the mixture was stirred under nitrogen gas at 80C for 18 hours. The reaction mixture was cooled and the solvent was removed under reduced pressure. Ethyl acetate was added and the organic layer was washed with water. The organic layer was dried, filtered and the solvent was removed under reduced pressure. The product was used in the next step without further purification. | |
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); XPhos; In 1,4-dioxane; water; at 80℃; for 18h;Inert atmosphere; | Preparation of Intermediate 63 A mixture of 1,4-dioxane and water (3:1, 9.36 ml) was degassed by bubbling nitrogen gas through the mixture. Intermediate 62 (2.00 g, 3.12 mmol), [3-(tert-butoxycarbonylamino)phenyl]boron ic acid (780 mg, 3.28 mmol), tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.06 mmol), 2-dicyclohexylphosphino-2?,4?,6?-triisopropylbiphenyl (Xphos) (119 mg, 0.25 mmol) and potassium phosphate tribasic (3.307 g, 5 eq.) were added and the mixture was stirred under nitrogen gas at 80 C. for 18 hours. The reaction mixture was cooled and the solvent was removed under reduced pressure. Ethyl acetate was added and the organic layer was washed with water. The organic layer was dried, filtered and the solvent was removed under reduced pressure. The product was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | Example 50 tert-butyl 3-(4-amino-1-methyl-1H-pyrazol-5-yl)phenylcarbamate To a 10 mL microwave vial was added 5-chloro-1-methyl-4-nitro-1H-pyrazole from Example 1 (150 mg, 0.93 mmol), <strong>[380430-68-2]3-(tert-butoxycarbonylamino)phenylboronic acid</strong> (440 mg, 1.86 mmol), dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) (152 mg, 0.019 mmol), a 1:1 M solution of Na2CO3/KOAc (1 mL) and acetonitrile (4 mL). The mixture was irradiated to 130 C. with a microwave for 40 min and the mixture was cooled, concentrated and purified via flash chromatography, heptane/ethyl acetate 20% to 95% to afford a yellow oil. To a 50 mL round bottom flask was added the nitro compound (120 mg, 0.90 mmol), iron (156 mg, 2.8 mmol), ammonium chloride (200 mg, 3.7 mmol), ethanol (10 mL) and water (1.5 mL). The mixture was stirred for 1 h and the reaction was monitored by LCMS. Upon completion of the reaction, the mixture was filtered through a pad of Celite and was washed with ethyl acetate (30 mL) and a 10% aqueous solution of K3PO4 (30 mL). The organic layer was washed with water (30 mL), dried over Na2SO4 and the organic solvent was distilled off to yield tert-butyl 3-(4-amino-1-methyl-1H-pyrazol-5-yl)phenylcarbamate as a brown oil with a purity of >98% (120 mg, 45%) over two steps. ESIMS m/z=289.1 (M+1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | 3-(7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)aniline [0676] To a round-bottom flask, 4-(4-chloro-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole (S13, 347 mg, 1 mmol) and (3-Boc-aminophenyl) bronoic acid (711 mg, 3 mmol), 1,2-dimethoxyethane (20 mL), and Na2CO3 (2 M, 5 mL) were added. The system was degassed to remove oxygen and nitrogen was refilled. Pd(dppf)Cl2-CH2Cl2 (81 mg, 0.1 mmol) was added and the system was degassed and refilled with nitrogen. The reaction mixture was heated at reflux for 16 h. The reaction was quenched with water and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and the volatile components were removed on a rotary evaporator. The residue was dissolved in CH2Cl2 (4 mL) and CF3CO2H (4 mL) was added. The reaction was stirred for 1 h before the volatile components were removed on a rotary evaporator. The remaining residue was purified by reverse HPLC to afford the title product as a salt of CF3CO2H (80 mg, 16% yield). 1H NMR (MeOD-d4, 300 MHz): 7.74 (t, J=7.82 Hz, 1H), 7.70-7.60 (m, 2H), 7.55 (s, 1H), 7.47 (dd, J=8.04, 1.12 Hz, 1H), 7.36 (s, 1H), 3.72 (s, 3H), 2.96 (s, 3H), 2.30 (s, 3H), 2.12 (s, 3H). ESI-MS calculated for C23H22N5O2 [M+H]+=400.18; Observed: 401.00. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With tetrakis(triphenylphosphine) palladium(0); copper(I) thiophene-2-carboxylate; In tetrahydrofuran; for 4h;Inert atmosphere; Reflux; | General procedure: To the stirred solution of 1-(methylsulfanyl)-3,4-dihydroisoquinoline (1, 1.0 mmol, 0.18 g) in THF (10 mL)under argon atmosphere arylboronic acid (1.2 mmol), CuTC(3 equiv, 3.0 mmol, 0.57 g), and Pd(PPh3)4 (8 mol%, 0.08mmol, 92 mg) were added. The reaction was followed by TLC and HPLC-MS. The mixture was refluxed until the starting material disappeared. After cooling, the solvent was evaporated and CHCl3-MeOH (7:1) mixture (50 mL) wasadded. The crude reaction mixture was subsequently washed with 25% aq NH3 (2 × 25 mL). The aqueous layer was extracted with CHCl3-MeOH (7:1) mixture (2 × 25 mL).The combined organic phase was dried over Na2SO4 and the residue after evaporation purified by flash chromatography(silica gel 60 PF254) using CH2Cl2-MeOH as the eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With copper diacetate; triethylamine; In tetrahydrofuran; at 60℃; for 2h; | Synthesis of tert-butyl N-(3-(3-iodo-2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-1-yl)phenyl)carbamate A mixture of the compound of Reference Example 1 (750 mg, 2.5 mmol), N-tert-butoxycarbonyl-3-aminophenylboronic acid (1.5 g, 6.3 mmol), copper(ll) acetate (1.37 g, 7.5mmol) and triethylantine (4.3 mL, 31 mmol) in teirahydroftiran (THF) (50 mL) was stirred at60C for 2 h. The reaction mixture was diluted with an aqueous ammonia solution and insoluble material was filtered off The filtrate was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The organic layer was evaporated in vacuo and the residue was purified by silica gel column chromatography using n-heptane/ethyl acetate (3/7, v/v) togive the title compound (470 mg, 38% yield).?H-NMR (300 MHz, CDC13, ): 1.51 (s, 911), 6.66 (brs, 11-f), 7.09 (brd,J= 8.0 Hz, 1H), 7.15(t, J 4.9 Hz, 1H), 7.31 (bid, J= 8.0 F{z, 1H), 7.40 (t, J 8.0 F{z, 1H), 7.64 (brs, 1H), 8.63(d, J= 2.3 }-Iz, 1H), 8.69 (d,J= 4.9 Hz, 2H), 9.12 (d, J- 2.3 Hz, 1H).ESI-MS:m/z 491 M+H).HRMS (FAB) calcd for C20H201N403, 491.0580; found, 491.0554. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; at 150℃; for 0.166667h;Inert atmosphere; Microwave irradiation; | [00289] Into a reaction vial with magnetic stir bar was added 6-Chloro-2-(4-phenoxy- phenoxy)-nicotinamide (175.00 mg; 0.51 mmol; 1.00 eq.), 3-Boc-aminophenylboronic acid(146.09 mg; 0.62 mmol; 1.20 eq.), and [1,1?-bis(diphenylphosphino)ferrocene] dichloropalladium(ii), complex with dichloromethane (1:1) (41.94 mg; 0.05 mmol; 0.10 eq.). The vessel was evacuated and back-filled with nitrogen. Added [1,4]Dioxane (3.00 ml) and cesium carbonate (770.34 tl; 1.54 mmol; 3.00 eq.) and then evacuated and back-filled with nitrogen again. Stuffed at 150C in a microwave for 1 0mm. The reaction was concentrated, redissolved in ethyl acetate (3mL), loaded on silica gel and purified via flash chromatography (Biotage): 25g column using 25% ethyl acetate hexanes isocratic for 1mm then ramped to 50% ethyl acetate hexanes over 5mm at a flow rate of 25mLmin. The product fractions were combined and concentrated to afford tert-butyl (3-(5-carbamoyl-6-(4- phenoxyphenoxy)pyridin-2-yl)phenyl)carbamate (187mg, 73%) as a white solid.MS: m/z = 498 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
360 mg | With pyridine; copper diacetate; In dichloromethane; at 0 - 20℃; for 20h; | Step 88C[00271] To a mixture of 88b (200 mg, 0.82 mmol), 88c (390 mg, 1.64 mmol) in DCM (10 ml) at 0C was added Cu(OAc)2 (224 mg, 1.23 mmol) and pyridine (185 p1). The mixture stirred at rt for 20h. Water was added, extracted with EtOAc twice. The organic extracts were washed with brine, dried over Na2504, filtered, and concentrated. The residue was purified by silica gel chromatography to give 88d (360 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.4% | With palladium diacetate; potassium carbonate; triphenylphosphine; In 1,4-dioxane; water; at 120℃; for 0.5h;Microwave irradiation; | To a solution of I -[2-[4-(dimethylamino)-1 -piperidyl]ethylj-3-iodo-pyrazolo[3,4- djpyrimidin-4-amine (50 mg, 0.1205 mmcl) in dioxane/water (4.5/0.5 ml) was added 3- (boc-amino)benzeneboronic acid (1.5 eq., 42.9 mg, 0.181 mmol), potassium carbonate(1.5 eq., 25.0 mg, 0.181 mmol) and triphenylphosphine (20 mol %, 9.5 mg) followed by palladium acetate (5 mol %) and the mixture heated in the microwave at 120 C for 30 mins. The mixture was concentrated in vacuo and purified by column chromatography, MeOH/DCM (10% then 0-30 drops NEt3 per 100 ml) to give a cream solid, (28.0 mg, 0.0583 mmol, 48.4 %). 1H NMR (500 MHz, MeOD) oe 8.27 (a, 1 H), 7.88 (s, I H), 7.50 -7.44(m, 2H), 7.37(d, J= 7.0, IH), 4.57 (t, J= 6.7, 2H), 3.16-3.10 (m, 2H), 2.95 (t, J-6.7, 21-I), 2.35 (m, 7H),2.14 (t,J= 11.0, 2H), 1.88(d, J= 12.7,2H), 1.56(s, 9H), 1.47(m, 2H); 13C NMR (126 MHz, MeOD) a 158.42 (C), 155.37 (CH), 154.22 (C), 154.00(C), 144.97 (C), 140.14 (C), 133.30 (C), 129.46 (CH), 122.27 (CH), 119.16 (CH), 118.54(CH), 97.74 (C), 79.72 (C), 62.16 (CH), 56.21 (CH2), 52.29 (2x CH2), 44.06 (CH2), 40.16(2x CH3), 27.38 (2x CH2), 27.28 (3x CH3); MS (ES +ve) [M+H]: 481.4; KRMS (ES +ve),C25H37N802 [M+Hlt: calculated 480.30340, found 481.3054. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 120℃; for 1h;Microwave irradiation; | Step 1: Preparation of tert-Butyl (3-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)carbamate To a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (196 mg, 1.00 mmol) in 1,4-dioxane (7 mL) and water (3 mL) was added 3-boc-aminophenylboronic acid (237 mg, 1.00 mmol), potassium carbonate (414 mg, 3.00 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (36 mg, 0.05 mmol). The solution was treated with microwave radiation at 120 C. for one hour. After cooling the resulting mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, brine and dried over magnesium sulfate. The solution was filtered and concentrated in vacuo to provide the crude coupled product. The material was purified using normal phase chromatography (ethyl acetate/heptane) to provide tert-butyl (3-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)carbamate as a white solid (113 mg, 37% yield): MS (ES) m/z 310 (M+H). |
37% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 120℃; for 1h;Microwave irradiation; | To a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (196 mg, 1.00 mmol) in 1,4-dioxane (7 mL) and H2O (3 mL) was added 3-Boc-aminophenylboronic acid (237 mg, 1.00 mmol), K2CO3 (414 mg, 3.00 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]-dichloropalladium(II).DCM (36 mg, 0.05 mmol). The solution was treated with microwave radiation at 120 C. for one hour. After cooling the resulting mixture was partitioned between EtOAc and H2O. The organic layer was washed with H2O, brine and dried over MgSO4. The solution was filtered and concentrated in vacuo to provide the crude coupled product. The material was purified using normal phase chromatography (EtOAc/heptane) to provide the title compound as a white solid (113 mg, 37% yield): MS (ES) m/z 310 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; caesium carbonate; triphenylphosphine; In toluene; at 80℃; for 24h; | A solution of fluorene (1.0 equivalent) in tetrahydrofuran (THF) is added to a solution of lithium diisopropylamide (LDA) at -78 C. (1.0 equivalent). The mixture is allowed to warm slowly to 0 C., then re-cooled to -78 C. prior to the addition of methyl 3-(dimethylamino)propenoate (1.0 equivalent). The mixture is allowed to warm slowly to ambient temperature, quenched by addition of 1 N HCl, and extracted with ether. The extract is washed sequentially with 1 N HCl, saturated aqueous NaHCO3, and brine, then dried over mgSO4, filtered, and evaporated. The product ester is purified by chromatography on silica gel. (0469) A solution of the ester (1.0 equivalent) in THF is treated with excess lithium aluminum hydride, then quenched by addition of oxalic acid and extracted with ether. The extract is washed sequentially with 1 N HCl, saturated aqueous NaHCO3, and brine, then dried over mgSO4, filtered, and evaporated. The product alcohol is purified by chromatography on silica gel. (0470) The alcohol from above (1.0 equivalent) is oxidized to the aldehyde by reaction with Dess-Martin periodinane (1.5 equivalent) in dichloromethane solution. The solution is filtered and washed sequentially with 1 N HCl, saturated aqueous NaHCO3, and brine, then dried over mgSO4, filtered, and evaporated. The product aldehyde is purified by chromatography on silica gel. (0471) A mixture comprising the above-described aldehyde (1.0 equivalent), 3-(N-BOC-amino)phenylboronic acid (2.0 equivalents), Cs2CO3 (2.0 equivalents), Pd2(dba)3.CHCl3 (0.025 equivalent), and Ph3P (0.05 equivalent) in toluene is heated at 80 C. for 24 hours. After cooling to ambient temperature, the mixture is concentrated and the product is purified by chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium carbonate; In tetrahydrofuran; water; at 60℃; for 3h;Inert atmosphere; Sealed tube; | Under an argon atmosphere,To the reaction vessel was added 3 - ((tert-butoxycarbonyl) amino) phenylboronic acid benzofuran-2-ylboronic acid118.5 mg (0.5 mmol),6.6 mg (0.01 mmol) of dichloro [1,1'-bis (di-tert-butylphosphino) ferrocene] palladium,286 mg (1 mmol) of sodium carbonate decahydrate,0.5 mL (0.75 mmol) of a 1.5 M solution of (E) -1-chloro-3,3,3-trifluoropropene in tetrahydrofuran,0.5 mL of tetrahydrofuran and 0.18 mL of distilled water were added.After closing the reaction vessel,Followed by stirring at 60 C. for 3 hours.The mixture was purified by silica gel column chromatography (hexane: ethyl acetate = 25: 0 to 21: 4)(White solid, yield 72%) of (E) -2- (3,3,3-trifluoro-1-propen- 1 -yl) benzofuran. |
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