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[ CAS No. 57805-85-3 ]

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2D
Chemical Structure| 57805-85-3
Chemical Structure| 57805-85-3
Structure of 57805-85-3 *Storage: {[proInfo.prStorage]}

Quality Control of [ 57805-85-3 ]

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Product Details of [ 57805-85-3 ]

CAS No. :57805-85-3MDL No. :MFCD00466275
Formula : C10H9NO3 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :191.18Pubchem ID :674268
Synonyms :

Computed Properties of [ 57805-85-3 ]

TPSA : 65.5 H-Bond Acceptor Count : 4
XLogP3 : 2.4 H-Bond Donor Count : 1
SP3 : 0.10 Rotatable Bond Count : 2

Safety of [ 57805-85-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 57805-85-3 ]

  • Upstream synthesis route of [ 57805-85-3 ]
  • Downstream synthetic route of [ 57805-85-3 ]

[ 57805-85-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 34844-79-6 ]
  • [ 57805-85-3 ]
YieldReaction ConditionsOperation in experiment
65% With potassium <i>tert</i>-butylate In diethyl ether at 20℃; for 0.42 h; Inert atmosphere Compound 2 (2.62 g, 13.9 mmol, 1.00 eq.) was dissolvedin dried diethyl ether and poured into a flask in which an argon atmosphere was maintained. Then,potassium t-butoxide (0.78 g, 6.9 mmol, 0.50 eq.) was carefully added and the mixture stirred atroom temperature. After 25 min, several drops of water were added and the solvent evaporated.The remainder was mixed with water (30 mL) and the mixture extracted three times with 30 mL ofdiethyl ether. After drying by sodium sulfate, filtration, and the evaporation of ether, light yellowcrystals were obtained with a yield of 65percent; mp 94 °C. 1H-NMR: δ = 7.55 (d, J = 7.9, 1H, H4), 7.48–7.41(m, 2H, H7 and H6), 7.19–7.30 (m, 1H, H5), 5.00 (bs, 2H, NH2), 3.96 (s, 3H, COOCH3). 13C-NMR: δ = 162.1 (COOCH3), 154.3 (C7a), 138.9 (C3), 129.1 (C4), 125.6 (C3a), 122.5 (C5), 121.8 (C2), 119.8(C6), 112.8 (C7), 51.7 (COOCH3). MS (EI, 70 eV) Found: 191 (calculated for C10H9NO3: 191.19);m/z (percent) = 191 (M+, 100), 159 (50), 133 (25), 103 (90), 83 (20), 77 (50), 51 (25).
56% With NaH In dimethyl sulfoxide Methyl 3-aminobenzo[b]furan-2-carboxylate.
A solution of methyl 2-(2-cyanophenoxy) ethanoate (3.82 g, 20 mmol) in DMSO (40 mL) is added dropwise to a suspension of NaH (0.84 g, 21 mmol) and DMSO (10 mL) stirred under N2 at 25° C.
After 10 min the mixture is poured onto ice water and extracted with ether.
The combined extracts are washed with water, saturated brine and dried (MgSO4).
After removal of the solvent under reduced pressure, methyl 3-aminobenzo[b]furan-2-carboxylate (2.15 g, 56percent) is obtained as a yellow solid. 1 H NMR (DMSO) δ7.95 (1H, d, J=7.7 Hz), 7.48 (2H, d, J =3.4 Hz), 7.29-7.22 (1H, m), 6.40 (2H, brs), 3.80 (3H, s).
Reference: [1] Molecules, 2016, vol. 21, # 2,
[2] Journal of Medicinal Chemistry, 1999, vol. 42, # 26, p. 5464 - 5474
[3] Patent: US5679683, 1997, A
  • 2
  • [ 611-20-1 ]
  • [ 96-32-2 ]
  • [ 57805-85-3 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In acetone for 4.00 h; Heating / reflux Example 72: 3-Hvdroxy-lH-benzo[4,51furo[3,2-dlpyrimidine-2,4-dioneStep a.) 3-Amino-benzofuran-2-carboxylic acid methyl ester ort/zoe-Cyanophenol (5.0 g, 41.3 mmol) was placed in a round bottom flask followed by acetone (200 ml) and K2CO3 (6.8 g, 49 mmol). Next, methyl bromoacetate (3.91 ml, 41.3 mmol) was added dropwise at 2°C and the reaction was heated to reflux. After 4 hours, the reaction was filtered and the acetone was evaporated providing the title compound (7.32 g, 93 percent) as a white solid.
Reference: [1] Patent: WO2006/14647, 2006, A2. Location in patent: Page/Page column 51
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 7, p. 3209 - 3222
[3] Patent: KR2015/84657, 2015, A. Location in patent: Paragraph 1169
  • 3
  • [ 96-35-5 ]
  • [ 394-47-8 ]
  • [ 57805-85-3 ]
YieldReaction ConditionsOperation in experiment
48% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12.00 h; Heating / reflux Preparation Example 1: Preparation of 3-amino-benzofuran-2-carboxylic acid methyl ester0.22 g (1.18 mmol) of σ-fluorobenzonitrile was dissolved in 5 ml of N5N- dimethylformamide, 0.16 ml (2.18 mmol) of methyl glyconate and 0.62 g (4.54 mmol) of potassium carbonate were added thereto at room temperature, and the mixture was refluxed with heating for 12 hrs. After the reaction was completed, the reaction mixture was diluted with 10 ml of ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, and concentrated under a reduced pressure. The residue was subjected to silica gel column chromatography <n="19"/>(hexane:ethyl acetate = 4:1) to obtain the title compound (0.10 g, 48percent yield).1H NMR (300MHz, DMSO-d6): δ 3.97(s, 3H), 4.98(s, 2H), 7.23-7.28(m, IH), 7.44-7.47(m, 2H), 7.56(d, IH)Mass(m/e, M+): 192
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 22, p. 6362 - 6365
[2] Patent: WO2009/48274, 2009, A2. Location in patent: Page/Page column 16-17
  • 4
  • [ 611-20-1 ]
  • [ 57805-85-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 26, p. 5464 - 5474
[2] Molecules, 2016, vol. 21, # 2,
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