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Product Details of [ 142935-60-2 ]

CAS No. :142935-60-2 MDL No. :MFCD09925119
Formula : C10H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :XUTBNKYATQJDLC-UHFFFAOYSA-N
M.W : 176.17 Pubchem ID :23438892
Synonyms :

Calculated chemistry of [ 142935-60-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.76
TPSA : 50.44 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 1.79
Log Po/w (WLOGP) : 2.06
Log Po/w (MLOGP) : 1.11
Log Po/w (SILICOS-IT) : 2.08
Consensus Log Po/w : 1.74

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.44
Solubility : 0.639 mg/ml ; 0.00363 mol/l
Class : Soluble
Log S (Ali) : -2.47
Solubility : 0.6 mg/ml ; 0.0034 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.06
Solubility : 0.153 mg/ml ; 0.000867 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.01

Safety of [ 142935-60-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 142935-60-2 ]

* 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 [ 142935-60-2 ]

[ 142935-60-2 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 69999-16-2 ]
  • [ 142935-60-2 ]
YieldReaction ConditionsOperation in experiment
44% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 0℃; for 3.0h;Heating / reflux;Product distribution / selectivity; N-bromosuccinimide (0.89 g, 5.0 mmol) was added to a solution of 2,3- dihydrobenzofuran-5-ylacetic acid (0.89 g, 5.0 mmol) and benzoyl peroxide (lOmg) in carbon tetrachloride (100 mL) and refluxed for 3 hours. The mixture was cooled to room temperature, filtered and concentrated. The product was recrystallized from ethyl acetate: hexane (2:1) to give a 0.39 g (44%) of white solid. 1H NMR (400 MHz, CD3OD) 5 7.62 (d, J = 2.4 Hz, IH), 7.52 (d, J = 0.8 Hz, IH), 7.46 (d, /= 8.4 Hz, IH), 7.21 (dd, J= 1.6, 8.4 Hz, IH), 6.74 (d, J = 3.2 Hz, IH), 3.74 (s, 2H).; a) Benzofuran-5-yl-acetic acidTo the solution of (2,3-dihydro-benzofuran-5-yl)-acetic acid (0.89 g, 5 mmol) and N- bromosuccinimide (0.89 g, 5 mmol) in carbon tetrachloride (10 mL) was added 10 mg of benzoyl peroxide. The mixture was refluxed for 3 h and cooled with ice. The solid was removed by filtration, the filtrate was concentrated, the residue was crystallized from 1:1 ethyl acetate: hexane to give a white solid (390 mg, 44%). 1H NMR (400 MHz, CDCl3) 5 10.5 (b s, IH), 7.62 (d, J = 2.2 Hz, IH), 7.52 (d, J = 1.4 Hz, IH), 7.46 (d, J = 8.4 Hz, IH), 7.21 (dd, J = 8.4, 1.8 Hz, IH), 6.74 (d, J = 2.2 Hz, IH), 3.75 (s, 2H).
  • 2
  • [ 142935-60-2 ]
  • ((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-amine; hydrochloride [ No CAS ]
  • 2-Benzofuran-5-yl-N-((R)-5-methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-N-methyl-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 18h; Ambient temperature;
  • 3
  • [ 142935-60-2 ]
  • (2-Benzofuran-5-yl-ethyl)-((R)-5-methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole / tetrahydrofuran / 18 h / Ambient temperature 2: BH3*THF / tetrahydrofuran / 5 h / Heating
  • 4
  • [ 142935-60-2 ]
  • C10H7ClO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride 2-Benzofuran-5-yl-N-{1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl}-N-(4- fluorobenzyl) acetamide, tartrate [(128NLS22-A).] [BENZOFURAN-5-YL-ACETIC] acid was prepared adapting a procedure by Dunn et al. [(J.] Med. Chem., 1986, [29,] 2326) and converted into the corresponding acetyl chloride by treatment with oxalylchloride. The title compound was prepared from [118AF52-95 (58] mg, 0.18 mmol) following the same method as described for 117NLS87-A. Yield: 27 mg, 43%. Rf= 0.52 [(MEOH/CH2CL2 1] : 9). LCMS [M/Z] 481 [[M+H]] [+. IH-NMR (CDC13,] rotamers 0.6 : 0.4) 8 7.64-6. 68 (m, 9H, Ar-H), 4.62-4. 54 (m, 0.6H, pip-H) 4.53-4. 44 (m, 3H, dioxane- H, benzyl-H), 4.07-4. 03 (m, 2H, dioxane-H), 3.82-3. 61 (m, 3.2H, pip-H, benzyl-H, [DIOXANE-H),] 3.45 (s, 1.2H, benzyl-H), 2.91-2. 80 (m, 2H, pip-H), 2.44-2. 35 (m, 2H, [NCH2),] 2.08-1. 98 (m, 2.2H, dioxane-H, pip-H), 1.85-1. 56 (m, 6H, pip-H, [NCH2CH2),] 1.32-1. 27 (m, 1. 8H, dioxane-H, pip-H). HPLC tR = 6.6 min.
  • 5
  • [ 7252-83-7 ]
  • [ 156-38-7 ]
  • [ 142935-60-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydroxide; PPA; toluene-4-sulfonic acid In ethanol; dimethyl sulfoxide; benzene 2.a 2a 2a Benzofuran-5-acetic Acid 5 g (0.033 mol) of 4-hydroxyphenylacetic acid are mixed in 30 ml of DMSO (dimethyl sulfoxide) and 5.7 ml of a 50% aqueous NaOH solution are added thereto. After 10 minutes at ambient temperature, 5.16 ml (0.033 mol) of bromoacetaldehyde dimethylacetal are added thereto and heated at 110° C. for 4 hours. The mixture is run into 1N hydrochloric acid and extracted with diethyl ether, the organic phase is dried over sodium sulfate and, after filtration, the solvent is evaporated off. 7.85 g (0.029 mol) of the product thus obtained are mixed in 50 ml of absolute ethanol and 1.5 mmol of p-toluenesulfonic acid are added thereto. The mixture is refluxed for 3 hours. The ethanol is evaporated off, the remainder is taken up with a 5% NaHCO3 solution until a neutral pH is obtained, the organic phase is dried over sodium sulfate and, after filtration, the solvent is evaporated off. 6.57 g of polyphosphoric acid are refluxed with 40 ml of benzene and, after 15 minutes, 7.06 g of the product obtained above, dissolved in 4 ml of benzene are added thereto and the mixture is refluxed for one hour. The benzene is removed, and the residue is washed with water, with a saturated NaHCO3 solution and with a saline solution. The title product is obtained, which is purified by flash chromatography, eluding with a 9/1 hexane/ethyl acetate mixture. 0.93 g of the title product are thus obtained.
YieldReaction ConditionsOperation in experiment
32.C.B Step B Step B Preparation of benzofuran-5-ylacetic acid 1.20 gm (6.3 mmol) of material prepared as described in Step A above was treated with 2N NaOH (6.5 ml) and MeOH (10 ml) at room temperature for 3 hr. The reaction mixture was then diluted with H2 O and the resultant solution was washed with Et2 O. The aqueous layer was acidified and extracted twice with EtOAc. The combined EtOAc layers were dried over Na2 SO4, filtered and evaporated to dryness to give 1.1 gm (6.25 mmol) of the title compound suitable for direct use in the next step.
  • 7
  • [ 121638-36-6 ]
  • [ 142935-60-2 ]
YieldReaction ConditionsOperation in experiment
59.1% With water; sodium hydroxide In methanol at 25 - 30℃; 4 Example 4: Preparation of 2,3-benzofuran-5-acetic acid (compound 16) Add 1000g of methanol to the reaction flask,Another 230 g (1.209 mol) of compound 15 was added.Stir to completely dissolve;Temperature control at 58 °C (1.450 mol) at 25-30 °CAn aqueous solution of sodium hydroxide;Incubation at about 30 °C reaction 2 ~ 4hr.After confirming the reaction,Concentrate methanol,Add 800g of water to the residue,Stir and dissolve.The temperature is controlled by adding 150g (about 1.60mol) concentrated hydrochloric acid at 25-30°C.Then add 600g of ethyl acetate to stir and extract.The aqueous phase is extracted once more with 200 g of ethyl acetate;Combine the organic phase,Dry with anhydrous sodium sulfate;concentrate,208 g of oil are obtained.600 g of ethyl acetate was added to the resulting oil to completely dissolve it.Then add 500g n-hexane,Stir thoroughly,Cool crystallization,filter,126 g of a solid is obtained (theoretical amount: 213.03 g);Yield:59.1%.
With sodium hydroxide In methanol 9.B Step B Step B Preparation of benzofuran-5-ylacetic acid Methyl benzofuran-5-ylacetate (1.2 gm, 6.3 mmol) was dissolved in methanol (10 mL) and 2N sodium hydroxide (6.5 mL) was added under nitrogen and the mixture was stirred at rt for 3 hr. It was then diluted with water and extracted with ether. The aqueous layer was acidified with 2N hydrochloric acid and again extracted twice with ethyl acetate. The organic layers were washed with brine, combined, dried over sodium sulfate and evaporated to give 1.1 gm of title compound suitable for the next step.
With sodium hydroxide In methanol 10.B Step B Step B Preparation of benzofuran-5-ylacetic acid Methyl benzofuran-5-ylacetate (1.2 gm, 6.3 mmol) was dissolved in methanol (10 mL) and 2N sodium hydroxide (6.5 mL) was added under nitrogen and the mixture was stirred at rt for 3 hr. It was then diluted-with water and extracted with ether. The aqueous layer was acidified with 2N hydrochloric acid and again extracted twice with ethyl acetate. The organic layers were washed with brine, combined, dried over sodium sulfate and evaporated to give 1.1 gm of title compound suitable for the next step.
  • 8
  • (1R)-1-{5-[(2,2,2-trifluoroethyl)oxy]pyridin-2-yl}ethylamine dihydrochloride [ No CAS ]
  • [ 142935-60-2 ]
  • [ 1146323-49-0 ]
YieldReaction ConditionsOperation in experiment
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; 1 To a small vial equipped with a magnetic stir bar were added 1 -benzofuran-5 - ylacetic acid (Meyer, M. D. et. al. J Med. Chem.1997, 40, 1049.) (29 mg, 0.17 mmol), (IR)-I- {5-[(2,2,2-trifluoroethyl)oxo]pyridin-2-yl}ethylamine dihydrochloride (48 mg, 0.17 mmol), 1- (3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (35 mg, 0.18 mmol), l-hydroxy-7- azabenzotriazole (25 mg, 0.18 mmol) and diisopropylethylamine (0.072 ml, 0.41 mmol) into 0.5 ml of DMF. The resulting solution was stirred at room temperature for 1 hour. The reaction mixture was purified by reverse-phase HPLC to give 2-(l-benzofuran-5-yl)-iV-{(li?)-l-[5-(2,2,2- trifluoroethoxy)pyridin-2-yl]ethyl}acetamide as a TFA salt. 1H NMR (CDCl3, 400 MHz) δ 8.25 (d, J= 2.4 Hz, IH), 7.62 (d, J= 2.0 Hz,lH), 7.49 (d, J= 1.2 Hz, IH), 7.46 (d, J= 8.4 Hz, IH), 7.35 (dd, J= 2.8, 8.4 Hz, IH), 7.30 (d, J= 8.8, IH), 7.26 (s, IH), 7.19 (dd, J= 1.6, 8.8 Hz, IH), 7.10 (d, J= 6.8 Hz, IH), 6.73 (dd, J= 0.8, 2.0 Hz, IH), 5.12 (quintet, J= 7.2 Hz, IH), 4.39 (q, J = 8.0 Hz, 2H), 3.66 (s, 2H), 1.43 (d, J= 6.8 Hz, 3H); HRMS (ES) [M+l]+ calcd for C19Hi8F3N2O3: 379.1264, Found: 379.1260.
  • 9
  • [ 133745-75-2 ]
  • [ 142935-60-2 ]
  • N-(benzofuran-5-ylmethyl)-N-(phenylsulfonyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With copper(l) iodide; N,N`-dimethylethylenediamine In 1,2-dichloro-ethane at 80℃; for 24h; Sealed tube; Inert atmosphere; regioselective reaction;
  • 10
  • [ 156-38-7 ]
  • [ 142935-60-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium iodide; sodium hydroxide / dimethyl sulfoxide / 50 - 80 °C 2: toluene-4-sulfonic acid / Reflux; Large scale 3: polyphosphoric acid / toluene / 105 - 110 °C 4: sodium hydroxide; water / methanol / 25 - 30 °C
  • 11
  • 4-((2,2-dimethoxy)ethoxy)phenylacetic acid [ No CAS ]
  • [ 142935-60-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / Reflux; Large scale 2: polyphosphoric acid / toluene / 105 - 110 °C 3: sodium hydroxide; water / methanol / 25 - 30 °C
  • 12
  • methyl 4-((2,2-dimethoxy)ethoxy)phenylacetate [ No CAS ]
  • [ 142935-60-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: polyphosphoric acid / toluene / 105 - 110 °C 2: sodium hydroxide; water / methanol / 25 - 30 °C
  • 13
  • [ 142935-60-2 ]
  • [ 69999-16-2 ]
YieldReaction ConditionsOperation in experiment
82.1% With hydrogen; sodium hydroxide; In methanol; water; at 60 - 65℃; under 6080.41 - 7600.51 Torr; Put 200g of methanol,400g water,24g sodium hydroxide was added to the reaction flask,Then add 100 g (567.6 mmol) of compound 16,Stir to completely dissolve;Transferred to the high pressure reactorThen add 20g Raney Ni,Nitrogen replacement,Into the hydrogen,Heat to 60-65C,Keep the hydrogen pressure in the kettle at 8~10atm;It reacts until it does not absorb hydrogen.After confirming the reaction,Remove the catalyst by filtration300 g of water was added to the resulting filtrate.Then concentrate the methanol under reduced pressure. After the basic concentration of methanol is complete,After cooling to 25 to 30C, 65 g (about 0.65 mol) of concentrated hydrochloric acid was added dropwise.Precipitation of solids,After cooling and crystallization,filter,83 g of a solid is obtained (theoretical amount: 101.15 g);Yield:82.1%.
  • 14
  • [ 142935-60-2 ]
  • [ 87776-76-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide; hydrogen / methanol; water / 60 - 65 °C / 6080.41 - 7600.51 Torr 2: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 10 °C / Reflux
  • 15
  • [ 142935-60-2 ]
  • [ 127264-14-6 ]
  • 16
  • [ 1158745-04-0 ]
  • [ 142935-60-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-ethynylbenzo[b]furane With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: With 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran for 2h; Stage #3: With oxone In acetone at 50℃; for 12h; 7 Example 7 At -78 ° C, n-butyllithium (2.4 mL, 2.5 mol / L, 1.2 equivalents) was added dropwise to a tetrahydrofuran solution (15 mL) of benzofuran-5-acetylene (710.8 mg, 1.0 equivalent), and reacted for 1 h. Then isopropanol pinacol borate (1.2 mL, 1.2 equivalents) was added dropwise to the mixed solution, The reaction was continued for 2h, quenched by the addition of a 1,4-dioxane solution of hydrogen chloride (1.9mL, 4M indioxane, 1.5 equivalents), and the reaction was warmed to room temperature. After the solvent was rotary evaporated, it was prepared into an acetone solution (0.3M), A potassium peroxymonosulfonate solution (0.5M, 4.6107 g, 1.5 equivalents) was added, transferred to 50 ° C. and stirred for 12 h, and isolated and purified to obtain 449.2 mg of 5-benzofuranacetic acid with a purity of 51%.
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 °C / Inert atmosphere 2.1: oxone||potassium monopersulfate triple salt; water / acetone / 12 h / 50 °C / Inert atmosphere
  • 17
  • C16H17BO3 [ No CAS ]
  • [ 142935-60-2 ]
YieldReaction ConditionsOperation in experiment
449 mg With oxone||potassium monopersulfate triple salt; water In acetone at 50℃; for 12h; Inert atmosphere;
  • 18
  • [ 142935-60-2 ]
  • 2-(benzofuran-5-yl)propanal [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: acetyl chloride / 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C 2.2: -78 - 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C 4.1: pyridinium chlorochromate; silica gel / dichloromethane / 2 h / 20 °C
  • 19
  • [ 142935-60-2 ]
  • C11H12O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: acetyl chloride / 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C 2.2: -78 - 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C
  • 20
  • [ 142935-60-2 ]
  • methyl 2-(benzofuran-5-yl)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetyl chloride / 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C 2.2: -78 - 20 °C
  • 21
  • [ 142935-60-2 ]
  • methyl (S)-4-(2-(benzofuran-5-yl)-1-oxopropan-2-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetyl chloride / 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C 2.2: -78 - 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C 4.1: pyridinium chlorochromate; silica gel / dichloromethane / 2 h / 20 °C 5.1: (R)-N-allyl-N-((S)-(3,5-di(naphthalen-1-yl)phenyl)(2-(di-tert-butylphosphaneyl)-4,5-bis(dimethylamino)phenyl)methyl)-2-methylpropane-2-sulfinamide; palladium(II) trifluoroacetate; silver fluoride; caesium carbonate / dibutyl ether / 48 h / 35 °C / Inert atmosphere
  • 23
  • [ 17138-28-2 ]
  • [ 142935-60-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 17 h / 100 °C 2: PPA / toluene / 3 h / 80 °C / Inert atmosphere 3: lithium hydroxide monohydrate; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C
  • 24
  • [ 142935-50-0 ]
  • [ 142935-60-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: PPA / toluene / 3 h / 80 °C / Inert atmosphere 2: lithium hydroxide monohydrate; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C
  • 25
  • [ 142935-51-1 ]
  • [ 142935-60-2 ]
YieldReaction ConditionsOperation in experiment
95% With lithium hydroxide monohydrate; lithium hydroxide monohydrate In tetrahydrofuran; methanol at 20℃; for 2h; 2.3 Step 3: To a stirred solution of ethyl 2-(benzofuran-5-yl)acetate (7-4) (4 g, 19.6 mmol, 1.0 eq.) in THF (20 mL) , MeOH (20 mL) was added followed by addition of lithium hydroxide (1.4 g, 58.82 mmol, 3.0 eq.) in water (20 mL). Reaction was stirred atRT for 2 hrs. After the completion [Monitored with TLC, Mobile Phase 60% EtOAc-Hexane], excess solvent was evaporated and acidified with 1(N) HCL in ice cooling condition and extracted with 10 % MeOH in DCM. Organic part was washed with saturated solution of NaCl, dried over anhydrous magnesium sulphate and concentrated under vacuum to afford 2-(benzofuran-5-yl)acetic acid (7-5) (3.3 g, 95%) as an off white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.28 (s, 1H), 7.96 (d, J = 2.0 Hz, 1H), 7.52 (d, J = 8.68 Hz, 2H), 7.20-7.18 (m, 1H), 6.92 (bs, 1H), 3.64 (s, 2H).
95% With lithium hydroxide monohydrate; lithium hydroxide monohydrate In tetrahydrofuran; methanol at 20℃; for 2h; 2.3 Step 3: To a stirred solution of ethyl 2-(benzofuran-5-yl)acetate (7-4) (4 g, 19.6 mmol, 1.0 eq.) in THF (20 mL) , MeOH (20 mL) was added followed by addition of lithium hydroxide (1.4 g, 58.82 mmol, 3.0 eq.) in water (20 mL). Reaction was stirred atRT for 2 hrs. After the completion [Monitored with TLC, Mobile Phase 60% EtOAc-Hexane], excess solvent was evaporated and acidified with 1(N) HCL in ice cooling condition and extracted with 10 % MeOH in DCM. Organic part was washed with saturated solution of NaCl, dried over anhydrous magnesium sulphate and concentrated under vacuum to afford 2-(benzofuran-5-yl)acetic acid (7-5) (3.3 g, 95%) as an off white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.28 (s, 1H), 7.96 (d, J = 2.0 Hz, 1H), 7.52 (d, J = 8.68 Hz, 2H), 7.20-7.18 (m, 1H), 6.92 (bs, 1H), 3.64 (s, 2H).
  • 26
  • [ 142935-60-2 ]
  • 1-(benzofuran-5-yl)butan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.08 h / 20 °C 1.2: 20 °C 2.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
  • 27
  • [ 142935-60-2 ]
  • 1-(benzofuran-5-yl)-N-methylbutan-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.08 h / 20 °C 1.2: 20 °C 2.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 3.1: glacial acetic acid / methanol / 0.25 h 3.2: 17 h / 20 °C
  • 28
  • [ 142935-60-2 ]
  • tert-butyl (1-(benzofuran-5-yl)butan-2-yl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.08 h / 20 °C 1.2: 20 °C 2.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 3.1: glacial acetic acid / methanol / 0.25 h 3.2: 17 h / 20 °C 4.1: triethylamine / dichloromethane / 0 - 20 °C
  • 29
  • [ 142935-60-2 ]
  • C18H25NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.08 h / 20 °C 1.2: 20 °C 2.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 3.1: glacial acetic acid / methanol / 0.25 h 3.2: 17 h / 20 °C 4.1: triethylamine / dichloromethane / 0 - 20 °C 5.1: isopropylamine / ethanol; methanol; hexane / Supercritical conditions; Resolution of racemate
  • 30
  • [ 142935-60-2 ]
  • C18H25NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.08 h / 20 °C 1.2: 20 °C 2.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 3.1: glacial acetic acid / methanol / 0.25 h 3.2: 17 h / 20 °C 4.1: triethylamine / dichloromethane / 0 - 20 °C 5.1: isopropylamine / ethanol; methanol; hexane / Supercritical conditions; Resolution of racemate
  • 31
  • [ 142935-60-2 ]
  • [1-(1-benzofuran-5-yl)butan-2-yl](methyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.08 h / 20 °C 1.2: 20 °C 2.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 3.1: glacial acetic acid / methanol / 0.25 h 3.2: 17 h / 20 °C 4.1: triethylamine / dichloromethane / 0 - 20 °C 5.1: isopropylamine / ethanol; methanol; hexane / Supercritical conditions; Resolution of racemate 6.1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C
  • 32
  • [ 142935-60-2 ]
  • [1-(1-benzofuran-5-yl)butan-2-yl](methyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.08 h / 20 °C 1.2: 20 °C 2.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 3.1: glacial acetic acid / methanol / 0.25 h 3.2: 17 h / 20 °C 4.1: triethylamine / dichloromethane / 0 - 20 °C 5.1: isopropylamine / ethanol; methanol; hexane / Supercritical conditions; Resolution of racemate 6.1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C
  • 33
  • [ 6638-79-5 ]
  • [ 142935-60-2 ]
  • 2-(benzofuran-5-yl)-N-methoxy-N-methylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: benzofuran-5-yl-acetic acid With benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: O,N-dimethyl-hydroxylamine hydrochloride In N,N-dimethyl-formamide at 20℃; 2.4 Step 4: To a stirred solution of 2-(benzofuran-5-yl)acetic acid (7-5) (3.3 g, 18.75 mmol, 1.0 eq.) in DMF (20 mL) were added DIPEA (9.8 mL, 56.25 mmol, 3.0 eq.) ,EDCI (3.93 g, 20.62 mmol, 1.1 eq.) and HOBT (3.79 g, 28.12 mmol, 1.5 eq.). Reaction was stirred at RT for 5 min followed by addition of weinreb amide (2 g, 20.62 mmol, 1.1 eq.). Reaction was stirred at RT for overnight. After the completion [Monitored with TLC, Mobile Phase 30% EtOAc-Hexane], reaction mixture was diluted with ethyl acetate (200 mL), washed 2-3 times with cold water. Organic phase was dried over magnesium sulphate and concentrated under reduced pressure to afford 2-(benzofuran-5-yl)-N-methoxy-N-methylacetamide (7-6) (4 g, 97%) as a light yellow sticky solid. 1H NMR (400 MHz, DMSO-d6) δ 7.95 (d, J = 2.08 Hz, 1H), 7.51-7.49 (m, 2H), 7.18 (dd, J = 1.36 Hz, 8.6 Hz, 1H), 6.91 (d, J=1.8 Hz, 1H), 3.80 (s, 2H), 3.67 (s, 3H), 3.11 (s, 3H).
97% Stage #1: benzofuran-5-yl-acetic acid With benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: O,N-dimethyl-hydroxylamine hydrochloride In N,N-dimethyl-formamide at 20℃; 2.4 Step 4: To a stirred solution of 2-(benzofuran-5-yl)acetic acid (7-5) (3.3 g, 18.75 mmol, 1.0 eq.) in DMF (20 mL) were added DIPEA (9.8 mL, 56.25 mmol, 3.0 eq.) ,EDCI (3.93 g, 20.62 mmol, 1.1 eq.) and HOBT (3.79 g, 28.12 mmol, 1.5 eq.). Reaction was stirred at RT for 5 min followed by addition of weinreb amide (2 g, 20.62 mmol, 1.1 eq.). Reaction was stirred at RT for overnight. After the completion [Monitored with TLC, Mobile Phase 30% EtOAc-Hexane], reaction mixture was diluted with ethyl acetate (200 mL), washed 2-3 times with cold water. Organic phase was dried over magnesium sulphate and concentrated under reduced pressure to afford 2-(benzofuran-5-yl)-N-methoxy-N-methylacetamide (7-6) (4 g, 97%) as a light yellow sticky solid. 1H NMR (400 MHz, DMSO-d6) δ 7.95 (d, J = 2.08 Hz, 1H), 7.51-7.49 (m, 2H), 7.18 (dd, J = 1.36 Hz, 8.6 Hz, 1H), 6.91 (d, J=1.8 Hz, 1H), 3.80 (s, 2H), 3.67 (s, 3H), 3.11 (s, 3H).
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