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Chemical Structure| 147404-69-1

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Product Details of [ 147404-69-1 ]

CAS No. :147404-69-1
Formula : C14H12O2
M.W : 212.24
SMILES Code : O=C(C1=CC(C2=CC=C(C)C=C2)=CC=C1)O
MDL No. :MFCD00452725
InChI Key :APYJGQZXCGXMGB-UHFFFAOYSA-N
Pubchem ID :2773978

Safety of [ 147404-69-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Application In Synthesis of [ 147404-69-1 ]

* 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.

  • Downstream synthetic route of [ 147404-69-1 ]

[ 147404-69-1 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 7383-90-6 ]
  • [ 147404-69-1 ]
  • 3
  • [ 585-76-2 ]
  • [ 5720-05-8 ]
  • [ 147404-69-1 ]
YieldReaction ConditionsOperation in experiment
98% General procedure: Bromobenzoic acid (0.5 g, 2.49 mmol) andpalladium acetate (1.15 mg, 0.005 mmol, 0.1 mol %) weredissolved in 15 ml of water under an argon atmosphere. After stirring for5 min at RT, p-tolylboronic acid (0.36 g,2.61 mmol) and KOH (0.42 g, 7.47 mmol) were added and it washeated to reflux for 5h. After cooling to RT, it was acidified with HCl and theproduct was extracted three times with methylene chloride. The combined organiclayers were dried over Na2SO4 and the solvent wasevaporated in vacuo. The crude product was purified by column chromatography onsilica gel with methylene chloride/methanol (9:1).
96% With potassium carbonate; In water; at 20.0℃; for 4h;Green chemistry; General procedure: A 50 mL flask was charged with an aryl halide (1.0 mmol), anaryl boronic acid (1.2 mmol), K2CO3 (2.0 mmol), nanocatalyst(0.05 mol% Pd) and deionized water (5 mL). The reactionwas stirred at room temperature for 4 h. The progress ofthe reaction was monitored by thin-layer chromatography After the reaction was completed, distilled water (25 mL) wasadded to the mixture and dilute 2 mol/L HCl was added dropwiseto pH 3.0-4.0 with stirring, and the mixture was heatedto 100 C for 10 min. The white solid that had formed wasfiltered off and washed with hot water. After drying, it wasdissolved in ether (5 mL) and was rapidly separated using asilica gel column. Elution with ether left behind small amountsof impurities and traces of palladium black to give a crudeproduct. The ether solution was evaporated to 3-5 mL andrecrystallized to obtain a pure product. All the products 3a-uare known compounds and were characterized by comparingtheir melting points and 1H NMR spectra with those preparedrecently by using a water-soluble glycine-based Pd catalyst,PdCl2(NH2CH2CO2H)2.10 The melting points and 1H NMRdata of 3a-u are listed in the supplemental material.
80% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 100.0℃; for 4h; General procedure: 3-bromobenzoic acid, the required aryl boronic acid (1.1 eq), K2CO3 (3 eq) and palladium(0) tetrakis(triphenylphosphine) are given in a screw-cap reactor, a 8:8: 1 toluene/EtOH/H2O mixture (8.5 mL/mmol 3-bromobenzoic acid) is added, the reactor is closed tightly and heated to 100C under stirring. After 4 h the mixture is cooled to room temperature, diluted with AcOEt (10 mL/mmol 3-bromobenzoic acid) and extracted with 5 % NaHCO3 (4x 10 mL/mmol 3-bromobenzoic acid). The pooled basic extracts are acidified to pH 3 by dropwise addition of concentrated HCI under stirring, then extracted with AcOEt (3x 10 mL/mmol 3-bromobenzoic acid). The pooled organic extracts are washed with water (10 mL/mmol 3-bromobenzoic acid) and brine (10 mL/mmol 3-bromobenzoic acid), dried over Na2SO4, filtered and evaporated to dryness under reduced pressure.
  • 5
  • [ 147404-69-1 ]
  • [ 306271-97-6 ]
  • 6
  • [ 147404-69-1 ]
  • C77H88Cl2O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% 53b) 4'-Methylbiphenyl-3-carboxylic acid To a solution of the compound (2.36 g) obtained in Working Example (53a) in tetrahydrofuran (20 ml) -water (10 ml) was added lithium hydroxide monohydrate (1.31 g). The mixture was stirred for 3 hours at room temperature. The reaction mixture was concentrated, diluted with water and washed with ethyl acetate. The aqueous layer was adjusted to pH 3 with 1N-HCl. Crystalline precipitate was collected by filtration and dried to afford the title compound as colorless needles (1.73 g, 78%), m.p.182-187 C. 1 H-NMR(200MHz,CDCl3) δ: 2.41(3H,s), 7.28(2H,d), 7.54(1H,t), 7.54(2H,d), 7.83(1H,m), 8.08(1H,td), 8.35(1H,t). IR(KBr)cm-1: 1700, 1450, 1415, 1310, 1300, 1270, 1260, 810, 755, 720.
  • 8
  • [ 841-77-0 ]
  • [ 147404-69-1 ]
  • 1-diphenylmethyl-4-(4'-methylbiphenyl-3-carbonyl)piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; thionyl chloride; In N-methyl-acetamide; n-heptane; dichloromethane; A. Preparation of (19) where --NR2 R3 represents Diphenylmethylpiperazine, R11 is 4-Methylphenyl, and R12 is Hydrogen To a suspension of <strong>[147404-69-1]4'-methylbiphenyl-3-carboxylic acid</strong> (2.2 g) in a mixture of methylene chloride (20 ml) and dimethylformamide (0.5 ml) was added thionyl chloride (1.48 g). The mixture was refluxed until the suspension dissolved, after which the temperature was allowed to cool to room temperature. To this solution was added 1-(diphenylmethyl)piperazine (3.94 g) in methylene chloride dropwise, and the reaction mixture allowed to stand overnight. Sodium hydroxide (30 ml of 1N) and 50 ml of methylene chloride was added, the organic layer separated, washed with brine, dried over sodium sulfate, and solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluding with 25% ethyl acetate in heptane, to yield 3.8 g of 1-diphenylmethyl-4-(4'-methylbiphenyl-3-carbonyl)piperazine. The dihydrochloride salt was prepared and recrystallized from ethanol, m.p. 226 C.
  • 9
  • [ 160417-31-2 ]
  • [ 147404-69-1 ]
YieldReaction ConditionsOperation in experiment
75% With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20.0℃; Ethyl 3-bromobenzoate (2.43 g) was mixed with p-methylphenylboronic acid (1.50 g), 2.12 g of sodium carbonate, 2.31 g of tetrakis(triphenylphosphine)palladium and 30 mL of water were added, and the mixture was stirred at reflux under nitrogen and stirred overnight. After cooling, the solution was evaporated by evaporation and the mixture was separated on a silica gel column (isolation system: petroleum ether:ethyl acetate = 10:1 to 5:1) to obtain 1.61 g of a coupling product in a yield of 71%. 2.26 g of the product in the previous step was added to a mixed solution of 20 mL of tetrahydrofuran and 5 mL of methanol. 100 mL of a 20% aqueous lithium hydroxide solution was added to the solution, and the mixture was stirred at room temperature overnight. After the completion of the process, the pH is adjusted to 2 with concentrated hydrochloric acid and the solvent is distilled off. The mixture was separated on a silica gel column (isolation system: petroleum ether:ethyl acetate=10:1 to 100% ethyl acetate) to obtain 1.59 g of a hydrolyzed product with a yield of 75%. The product of the previous step was directly added with 50 mL of thionyl chloride and stirred at reflux for 2 h. Thionyl chloride was distilled off to obtain the product of the acid chloride, which was used directly in the next step. 3.46 g of the acid chloride product and 2.29 g of the intermediate compound were mixed and 50 mL of pyridine was added. 100C, stirred at reflux overnight. After cooling, the solvent was distilled off and the mixture was separated on a silica gel column (isolation system: petroleum ether:ethyl acetate=10:1 to 100% ethyl acetate) to give a crude product. The crude product was purified by preparative chromatography (mobile phase: water (0.05% aqueous ammonia)-acetonitrile; B 40%-80%, 50 minutes) to give a pale orange solid 0.85 g, yield 20%.
With sodium hydroxide; In ethanol; water; A. Preparation of (18) where R11 is 4-Methylphenyl, and R12 is Hydrogen To a solution of ethyl 4'-methylbiphenyl-3-carboxylate (4.0 g) in ethanol (50 ml) was added a solution of 10 ml of 10% aqueous sodium hydroxide, and the mixture refluxed for 2 hours. Solvent was removed under reduced pressure, water added to the residue, and the solution filtered. The filtrate was acidified with dilute hydrochloric acid, and the white solid filtered off and dried under vacuum, yielding 2.4 g of 4'-methylbiphenyl-3-carboxylic acid m.p. 192 C.
  • 10
  • [ 147404-69-1 ]
  • 4'-methyl-biphenyl-3-carbonyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; for 2h;Reflux; Ethyl 3-bromobenzoate (2.43 g) was mixed with p-methylphenylboronic acid (1.50 g), 2.12 g of sodium carbonate, 2.31 g of tetrakis(triphenylphosphine)palladium and 30 mL of water were added, and the mixture was stirred at reflux under nitrogen and stirred overnight. After cooling, the solution was evaporated by evaporation and the mixture was separated on a silica gel column (isolation system: petroleum ether:ethyl acetate = 10:1 to 5:1) to obtain 1.61 g of a coupling product in a yield of 71%. 2.26 g of the product in the previous step was added to a mixed solution of 20 mL of tetrahydrofuran and 5 mL of methanol. 100 mL of a 20% aqueous lithium hydroxide solution was added to the solution, and the mixture was stirred at room temperature overnight. After the completion of the process, the pH is adjusted to 2 with concentrated hydrochloric acid and the solvent is distilled off. The mixture was separated on a silica gel column (isolation system: petroleum ether:ethyl acetate=10:1 to 100% ethyl acetate) to obtain 1.59 g of a hydrolyzed product with a yield of 75%. The product of the previous step was directly added with 50 mL of thionyl chloride and stirred at reflux for 2 h. Thionyl chloride was distilled off to obtain the product of the acid chloride, which was used directly in the next step. 3.46 g of the acid chloride product and 2.29 g of the intermediate compound were mixed and 50 mL of pyridine was added. 100C, stirred at reflux overnight. After cooling, the solvent was distilled off and the mixture was separated on a silica gel column (isolation system: petroleum ether:ethyl acetate=10:1 to 100% ethyl acetate) to give a crude product. The crude product was purified by preparative chromatography (mobile phase: water (0.05% aqueous ammonia)-acetonitrile; B 40%-80%, 50 minutes) to give a pale orange solid 0.85 g, yield 20%.
With pyridine; thionyl chloride; In toluene; 4'-Methyl-biphenyl-3-carboxylic acid (300 mg, 1.4 mmol) was added to a solution of thionylchloride (0.13 ml, 1.8 mmol) in toluene (3 ml) at O0C. After 2 min, pyridine (2 drops) was added, and stirring was continued overnight. After removal of the solvent and addition of dichloromethane (1.5 ml), 4-amino-l-hydroxymethyladamantane was added together with DIPEA (0.31 ml, 1.8 mmol). The mixture was stirred overnight and purified by preparative LC-MS to give the title compound as a mixture of two isomers. 1H NMR (400 MHz, CDCI3) δ:7.94 - 7.99 (m, 1 H), 7.65 - 7.74 (m, 2 H), 7.46 - 7.54 (m, 3 H), 7.25 - 7.30 (m, 2 H), 6.38 - 6.49 (m, 1 H), 4.15 - 4.28 (m, 1 H), 3.22 - 3.29 (m, 2 H), 2.41 (s, 3 H), 2.13 - 2.22 (m, 2 H), 2.00 - 2.06 (m, 1 H), 1.42 - 1.95 (m, 10 H).
  • 11
  • [ 585-76-2 ]
  • [ 195062-57-8 ]
  • [ 147404-69-1 ]
  • 12
  • [ 106-38-7 ]
  • [ 147404-69-1 ]
  • 14
  • [ 147404-69-1 ]
  • C25H24N2O2 [ No CAS ]
  • 15
  • [ 147404-69-1 ]
  • 4'-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-3-carboxylic acid [ No CAS ]
  • 16
  • [ 67-56-1 ]
  • [ 147404-69-1 ]
  • [ 114772-33-7 ]
YieldReaction ConditionsOperation in experiment
77% With sulfuric acid; for 5h;Reflux; General procedure: 4‘-Methyl-[1,1‘-biphenyl]-carboxylicacid (0.25 g, 1.18 mmol) was suspended with stirring in10 ml of abs. methanol. Subsequently, 0.13 ml of conc. H2SO4were added and the mixture was heated to reflux for 5h. After cooling to RT, 10ml of water were added and the product was extracted with methylene chloride.The combined organic layers dried over sodium sulfate and the solvent wasevaporated in vacuo. The crude product was purified by column chromatography onsilica gel with methylene chloride/methanol (95:5).
  • 17
  • [ 106-38-7 ]
  • [ 25487-66-5 ]
  • [ 147404-69-1 ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 100.0℃; for 4h; 186 mg 3-carboxyphenylboronic acid (1.05 mmol), 126 μ 4-bromotoluene (1.0 mmol), 417 mg K2CO3 (3.0 mmol) and 23 mg palladium(0) tetrakis(triphenylphosphine) (0.02 mmol) were given in a screw-cap reactor, 8.5 mL of a 8:8:1 toluene/EtOH/H2O mixture were added, the reactor was closed tightly and heated to 100C under stirring. After 4 h the mixture was cooled to room temperature, diluted with AcOEt (10 mL) and extracted with 2 % NaHCO3 (4x10 mL). The pooled basic extracts were acidified to pH 3 by dropwise addition of 6 N HCl under stirring and extracted with AcOEt (3x12 mL), the pooled organic extracts were washed H2O (10 mL) and brine (10 mL), then dried over Na2SO4, filtered and evaporated to dryness under reduced pressure. The crude product was purified by preparative HPLC, yielding 128 mg 3-(4'-tolyl)-benzoic acid (60 % yield).
  • 18
  • [ 111-49-9 ]
  • [ 147404-69-1 ]
  • azepan-1-yl(4'-methyl-[1,1'-biphenyl]-3-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% 185 mg 3-(4'-tolyl)-benzoic acid (0.87 mmol) were suspended in anhydrous DCM (5 mL) in a round-bottomed flask and 0.64 mL SOCI2 (8.7 mmol) were added. After 25 min a clear solution was obtained, which was stripped with argon. The residue was taken-up in anhydrous Et20 and stripped with argon 4 times, then evaporated to dryness under reduced pressure. The residue was taken-up in anhydrous DCM (5 mL) and 200 μ azepane (1.80 mmol) were given. After 20 min the mixture was concentrated under reduced pressure, taken-up with AcOEt (40 mL), washed with 5 % KHSO4 (2x15 mL), H2O (10 mL), 5 % NaHCO3 (2x15 mL) and brine (10 mL), then dried over Na2SO4, filtered and evaporated to dryness under reduced pressure. 250 mg product IV-c were obtained (97 % yield). LR-MS: m/z 294.3 ([M+H]+, clc 294.19).
  • 19
  • [ 141-91-3 ]
  • [ 147404-69-1 ]
  • (2,6-dimethylmorpholino)(4'-methyl-[1,1'-biphenyl]-3-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.5h; General procedure: To a suspension of the benzoic acid derivative obtained in step C1 in anhydrous DCM (5 mL/mmol) in a round-bottomed flask HOBt (1.1 1 eq) and EDC*HCI (1.10 eq) are added. After complete dissolution the required secondary amine (1.2 eq) and DIEA (1.5 eq) are added. After 30 min the mixture is concentrated under reduced pressure, taken-up with AcOEt (40 mL/mmol benzoic acid), washed with 5 % KHSO4 (2x15 mL/mmol benzoic acid), H20 (12 mL/mmol benzoic acid), 5 % NaHCO3 (3x12 mL/mmol benzoic acid) and brine (12 mL/mmol benzoic acid), dried over Na2SO4, filtered and evaporated to dryness under reduced pressure.
  • 20
  • [ 147404-69-1 ]
  • [ 476362-75-1 ]
  • N-hydroxy-5-((4'-methyl-[1,1'-biphenyl]-3-carboxamido)methyl)thiophene-2-carboxamide [ No CAS ]
  • 21
  • [ 24398-88-7 ]
  • [ 147404-69-1 ]
  • 22
  • [ 147404-69-1 ]
  • 3-(dimethylamino)-1-(4'-methyl-[1,1'-biphenyl]-3-yl)-2-(1-(p-tolyl)-1H-tetrazole-5-yl)prop-2-en-1-one [ No CAS ]
  • 23
  • [ 147404-69-1 ]
  • 4'-methyl-biphenyl-3-carboxylic acid (5-hydroxymethyladamantan-2-yl)amide [ No CAS ]
  • 4'-methyl-biphenyl-3-carboxylic acid (5-hydroxymethyladamantan-2-yl)amide [ No CAS ]
  • 24
  • [ 147404-69-1 ]
  • (6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methanamine trifluoroacetate [ No CAS ]
  • 4’-methyl-N-((6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)-[1,1’-biphenyl]-3-carboxamide [ No CAS ]
  • 25
  • [ 1613228-52-6 ]
  • [ 147404-69-1 ]
  • C37H36N6O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20.0℃; General procedure: Step1: 29a (0.10 g, 0.23 mmol), isoquinoline-6-carboxylic acid(0.044 g, 0.25 mmol) and HATU (0.174 g, 0.46 mmol) were dissolvedin 2 mL DMF, followed by the addition of DIEA (0.08 mL,0.46 mmol). The reaction was kept stirring at room temperatureovernight. The resulting mixture was partitioned between ethylacetate and saturated aqueous sodium bicarbonate. The organicswere washed with brine, dried over magnesium sulfate, concentratedand purified by column chromatography to yield yellowsolids (0.087 g, 64%).Step2The yellow solids (0.087 g, 0.14 mmol) produced in the laststep were suspended in2mLTFA and2mL DCM. The reaction wasstirred at room temperature for 2 h and concentrated in vacuum.The obtained solid was washed with diethyl ether, then gained thetitle compound 20 as a brown solid (0.030 g, 44%).
 

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