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Product Details of [ 619-44-3 ]

CAS No. :619-44-3 MDL No. :MFCD00016353
Formula : C8H7IO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DYUWQWMXZHDZOR-UHFFFAOYSA-N
M.W : 262.04 Pubchem ID :69273
Synonyms :

Calculated chemistry of [ 619-44-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.44
TPSA : 26.3 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) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.31
Log Po/w (XLOGP3) : 2.99
Log Po/w (WLOGP) : 2.08
Log Po/w (MLOGP) : 2.82
Log Po/w (SILICOS-IT) : 2.65
Consensus Log Po/w : 2.57

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.62
Solubility : 0.0629 mg/ml ; 0.00024 mol/l
Class : Soluble
Log S (Ali) : -3.21
Solubility : 0.163 mg/ml ; 0.000622 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.43
Solubility : 0.0983 mg/ml ; 0.000375 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.73

Safety of [ 619-44-3 ]

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

Application In Synthesis of [ 619-44-3 ]

* 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.

  • Upstream synthesis route of [ 619-44-3 ]
  • Downstream synthetic route of [ 619-44-3 ]

[ 619-44-3 ] Synthesis Path-Upstream   1~30

  • 1
  • [ 27329-70-0 ]
  • [ 619-44-3 ]
  • [ 53355-29-6 ]
YieldReaction ConditionsOperation in experiment
75% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere General procedure: A mixture of substituted iodobenzene (2 mmol), (5-formylfuran-2-yl)boronic acid (420 mg, 3mmol, 1.5 equiv), Pd(Ph3P)2Cl2 (0.1 mmol, 0.05 equiv, 70 mg) and potassium carbonate (6 mmol,3 equiv, 828 mg) in dioxone/H2O (6 mL/2 mL) was stirred at 100 °C under argon atmosphereuntil the starting material was consumed (typically 20 h). The reaction mixture was then diluted with 25 mL of saturated brine. The mixture was then extracted with EtOAc (25 mL × 2), and the organic layers were combined, dried over Na2SO4. The concentrated crude product was purifie dby column chromatography to afford c2a-e. The second step is the same as procedure A.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 6, p. 1024 - 1029
[2] Patent: CN106977474, 2017, A, . Location in patent: Paragraph 0034; 0037; 0038
[3] Chemical Biology and Drug Design, 2018, vol. 91, # 1, p. 257 - 268
  • 2
  • [ 1899-24-7 ]
  • [ 619-44-3 ]
  • [ 53355-29-6 ]
YieldReaction ConditionsOperation in experiment
78% With potassium phosphate In N,N-dimethyl acetamide at 60℃; for 24 h; Irradiation; Green chemistry General procedure: To a solution of 1 (0.3 mmol) and 2 (0.45mmol) in DMA (5 mL) was added 3wtpercent Pd/CeO2 (80 mg). The reaction mixture was stirred under incandescent light (0.79 Wcm-2) irradiation at 60°C for 24h. After reaction (monitored by TLC), when the reaction is complete, in test tube extraction and centrifugal separation allows for isolation of the desired product, while the catalyst can be washed with ethanol and water, dried under vacuum, and reused for the next run. After completion of the reaction (monitored by TLC), water (5 mL) was added and the mixture was extracted with EtOAc (3 × 5 mL). The combined organic phase was dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (10:1 petroleum ether/EtOAc) to give the target product.
Reference: [1] Chinese Chemical Letters, 2018, vol. 29, # 6, p. 903 - 906
  • 3
  • [ 619-44-3 ]
  • [ 378185-02-5 ]
  • [ 53355-29-6 ]
Reference: [1] Synthesis, 2001, # 11, p. 1681 - 1685
  • 4
  • [ 2689-65-8 ]
  • [ 619-44-3 ]
  • [ 53355-29-6 ]
Reference: [1] Synlett, 2005, # 2, p. 267 - 270
  • 5
  • [ 110-00-9 ]
  • [ 6018-41-3 ]
  • [ 18163-47-8 ]
  • [ 618-91-7 ]
  • [ 619-44-3 ]
  • [ 232264-73-2 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 50, p. 6608 - 6610
[2] Tetrahedron Letters, 2010, vol. 51, # 50, p. 6608 - 6610
  • 6
  • [ 6018-41-3 ]
  • [ 18163-47-8 ]
  • [ 618-91-7 ]
  • [ 619-44-3 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 50, p. 6608 - 6610
  • 7
  • [ 619-44-3 ]
  • [ 16819-43-5 ]
Reference: [1] Journal of Materials Chemistry, 2005, vol. 15, # 6, p. 690 - 697
  • 8
  • [ 64-17-5 ]
  • [ 619-44-3 ]
  • [ 51934-41-9 ]
Reference: [1] Inorganic Chemistry, 2017, vol. 56, # 22, p. 13962 - 13974
  • 9
  • [ 619-44-3 ]
  • [ 10602-00-3 ]
Reference: [1] Inorganic Chemistry, 2011, vol. 50, # 18, p. 9097 - 9105
[2] Journal of Materials Chemistry, 2011, vol. 21, # 36, p. 14041 - 14047
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9562 - 9575
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4851 - 4856
[5] Chinese Chemical Letters, 2015, vol. 26, # 6, p. 763 - 767
  • 10
  • [ 18293-53-3 ]
  • [ 201230-82-2 ]
  • [ 619-44-3 ]
  • [ 69316-08-1 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 4, p. 1118 - 1121
  • 11
  • [ 18293-53-3 ]
  • [ 619-44-3 ]
  • [ 13939-06-5 ]
  • [ 69316-08-1 ]
Reference: [1] Synthesis (Germany), 2012, vol. 44, # 18, p. 2885 - 2888
  • 12
  • [ 619-44-3 ]
  • [ 10602-04-7 ]
Reference: [1] Patent: CN106883217, 2017, A,
  • 13
  • [ 619-44-3 ]
  • [ 89976-27-2 ]
YieldReaction ConditionsOperation in experiment
74.71% at 20℃; for 5 h; Cooling with ice Methyl 4-iodo-3-nitrobenzoate
To an ice-cooled solution of methyl 4-iodobenzoate (8.0 g, 30.5 mmol) in conc. H2SO4 (57 mL), a solution of conc. HNO3 (45 mL) and conc. H2SO4 (38.0 mL) was added drop wise.
The reaction mixture was stirred at RT for 5 h, then quenched with ice, and extracted with ethyl acetate.
The organic layer was washed with saturated NaHCO3 and brine (50 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure.
The residue was recrystallized from DCM/n-hexane to yield the title compound as yellow solid (7.0 g, yield: 74.71percent).
33% at 0 - 40℃; for 6 h; A solution of 4-iodobenzoic acid methyl ester (5.24 g, 20.0 mmol) in sulfuric acid was treated with 1.43 mL of concentrated nitric acid in a dropwise fashion at 0 C. After 5 hours at room temperature, the reaction mixture was heated to 40 C for 1 hour. The resulting orange solution was added to 100 g of ice, treated with 200 mL of ethyl acetate, shaken for 30 minutes, and filtered. The phases were separated and the aqueous layer was extracted with 200 mL of ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was passed through a column of silica gel (100percent ethyl acetate) to give 2.0 g of 4-iodo-3- nitrobenzoic acid methyl ester as a yellow solid (33percent yield). A solution of 4-iodo-3-nitrobenzoic acid methyl ester (2.0 g, 6.50 mmol) in 25 mL of absolute alcohol and 15 mL of glacial acetic acid was treated with iron powder (3.6 g, 65.0 mmol) and the mixture was heated at 80 C. After 1 hour, the reaction mixture was filtered through a pad of silica, washed with ethanol, and concentrated in vacuo. The residue was diluted with a solution of potassium carbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 1.6 g of 3-amino-4-iodobenzoic acid methyl ester as a white solid (88percent yield). A solution of 3-amino-4-iodobenzoic acid methyl ester (1.59 g, 5.74 mmols) in 40 ML of dichloromethane was reacted with trifluoroacetic anhydride (3 mL, 21 mmol) at room temperature. After 30 minutes, the reaction mixture was concentrated in vacuo and the residue was taken up in cold water, filtered, and dried to give 2.1 g of the title product as an off-white solid (quantitative yield).
Reference: [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 5, p. 427 - 432
[2] Patent: US2016/333004, 2016, A1, . Location in patent: Paragraph 0420
[3] Patent: WO2005/30213, 2005, A1, . Location in patent: Page/Page column 189
[4] Journal of the Chemical Society, 1964, p. 1825 - 1835
  • 14
  • [ 610-97-9 ]
  • [ 619-44-3 ]
  • [ 55676-77-2 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 18, p. 7376 - 7379
[2] Chemistry Letters, 1993, # 3, p. 469 - 472
  • 15
  • [ 619-44-3 ]
  • [ 81290-20-2 ]
  • [ 1214788-34-7 ]
  • [ 23516-84-9 ]
YieldReaction ConditionsOperation in experiment
31%
Stage #1: With cesium fluoride In tetrahydrofuran at 0 - 20℃;
Stage #2: With hydrogenchloride; water In tetrahydrofuran for 5 h;
Preparation of Intermediate tert-butyld, 1, 1,3,3,3-hexafluoro-2-(4-iodψDhenyl)DroDan-2- yloxy)dimethylsilane (1 V-1); 4-lodobenzoic acid methyl ester (5g, 19.08mmol) dissolved in tetrahydrofuran (8OmL) and cooled to 00C. (Trifluoromethyl)trimethylsilane (5.43g, 38.2mmol) and cesium fluoride (145mg, 0.954mmol) added. Once addition was complete, reaction was warmed up to room temperature and stirred for 3 hours. Additional (trifluoromethyl)trimethylsilane (2.715g, 19.08mmol) was added and reaction stirred at room temperature for 4 hours. 4 M aqueous solution of hydrochloric acid (2OmL) added and stirred for 5 hours. The reaction mixture was diluted with ethyl acetate (500ml), washed with water (2x250ml), dried over sodium sulfate, filtered and concentrated. Crude purified on silica gel eluting with a gradient from 0percent to 10percent ethyl acetate in heptane to afford 2,2,2-trifluoro-1-(4-iodophenyl)ethanone (1.8g, 31 percent) GCMS= 300 at 1.47min and 1 ,1 ,1 ,3,3,3-hexafluoro-2-(4-iodophenyl)propan-2-ol (1.6g, 22percent); GCMS=370 at 1.60min.
31%
Stage #1: With cesium fluoride In tetrahydrofuran at 0 - 20℃;
Stage #2: With hydrogenchloride In tetrahydrofuran; water for 5 h;
4-Iodobenzoic acid methyl ester (5 g, 19.08 mmol) dissolved in tetrahydrofuran (80 mL) and cooled to 0° C. (Trifluoromethyl)trimethylsilane (5.43 g, 38.2 mmol) and cesium fluoride (145 mg, 0.954 mmol) added. Once addition was complete, reaction was warmed up to room temperature and stirred for 3 hours. Additional (trifluoromethyl)trimethylsilane (2.715 g, 19.08 mmol) was added and reaction stirred at room temperature for 4 hours. 4 M aqueous solution of hydrochloric acid (20 mL) added and stirred for 5 hours. The reaction mixture was diluted with ethyl acetate (500 ml), washed with water (2x250 ml), dried over sodium sulfate, filtered and concentrated. Crude purified on silica gel eluting with a gradient from 0percent to 10percent ethyl acetate in heptane to afford 2,2,2-trifluoro-1-(4-iodophenyl)ethanone (1.8 g, 31percent) GCMS=300 at 1.47 min and 1,1,1,3,3,3-hexafluoro-2-(4-iodophenyl)propan-2-ol (1.6 g, 22percent); GCMS=370 at 1.60 min.
Reference: [1] Patent: WO2010/86820, 2010, A1, . Location in patent: Page/Page column 46
[2] Patent: US2010/197591, 2010, A1, . Location in patent: Page/Page column 21
  • 16
  • [ 619-44-3 ]
  • [ 5467-74-3 ]
  • [ 89901-03-1 ]
YieldReaction ConditionsOperation in experiment
78% With sodium carbonate In ethanol; water; toluene at 80℃; for 4 h; Heating / reflux A mixture of methyl 4-iodobenzoate, 9.38g (35.8 mmol), 4- bromophenylboronic acid 7.18g (35.8 mmol), Pd (PPh3) 4,2. 07g (1.79 mmol), in 180ML of toluene and 100mL of ethanol was heated to obtain a clear solution. To the solution was added 30mL of 4. OM aq. NA2CO3. The reaction mixture refluxed for 4h at 80 °C. The mixture was cooled to room temperature and diluted with 300mL ethyl acetate. The organic layer was washed with 2X300ML portions of water, 2X300ML portions of sat. aq. NACL, and dried (MGSO4). After the solution was concentrated, the residue was purified by column chromatography (eluted with 7percent ETOAC-HEPTANE) to afford the desired product in 7. 8G (78percent) as a white SOLID. 1H NMR (CDC13) 8.10 (d, 2H, J = 9. 0HZ), 7.62 (d, 2H, J = 9. 0HZ), 7.59 (d, 2H, J = 9. 3HZ), 7.48 (d, 2H, J = 9.3 Hz), 3.95 (s, 3H).
78% With sodium carbonate In ethanol; water; toluene at 80℃; for 4 h; Heating / reflux Example 14. 4' -Bromo-biphenyl-4-carboxylic acid methyl ester.; A mixture of methyl 4-iodobenzoate, 9.38g (35.8 mmol), 4- bromophenylboronic acid 7.18g (35.8 mmol), Pd(PPh3)4, 2.07g (1.79 mmol), in 18OmL of toluene and 10OmL of ethanol was heated to obtain a clear solution. To the solution was added 3OmL of 4.0M aq. Na2CC>3. The reaction mixture refluxed for 4h at 80 °C. The mixture was cooled to room temperature and diluted with 30OmL ethyl acetate. The organic layer was washed with 2x300mL portions of water, 2x300mL portions of sat. aq. NaCl, and dried (MgSC>4) . After the solution was concentrated, EPO <DP n="96"/>the residue was purified by column chromatography (eluted with 7percent EtOAc-Heptane) to afford the desired product in 7.8g (78percent) as a white solid. 1H NMR (CDCl3) 8.10 (d, 2H, J = 9.0Hz)Λ 7.62 (d, 2H, J = 9.0Hz), 7.59 (d, 2H, J = 9.3Hz), 7.48 (d, 2H, J = 9.3 Hz) , 3.95 (s, 3H) .
78% With sodium carbonate In ethanol; water; toluene at 80℃; for 4 h; Example 96; 4' -Bromo-biphenyl-4-carboxylic acid methyl ester; A mixture of methyl 4-iodobenzoate, 9.38g (35.8 mmol), 4- bromophenylboronic acid 7.18g (35.8 mmol), Pd(PPh3) 4, 2.07g (1.79 mmol), in 18OmL of toluene and 10OmL of ethanol was heated to obtain a clear solution. To the solution was added 3OmL of 4.0M aq. Na2CO3. The reaction mixture refluxed for 4h at 80 °C. The mixture was cooled to room temperature and diluted with 30OmL ethyl acetate. The organic layer was washed with 2x300mL portions of water, 2x300mL portions of sat. aq. NaCl, and dried (MgSO4) . After the solution was concentrated, the residue was purified by column chromatography (eluted with 7percent EtOAc-Heptane) to afford the desired product in 7.8g (78percent) as a white solid.
78% With sodium carbonate In ethanol; water; toluene at 80℃; for 4 h; A mixture of methyl 4-iodobenzoate, 9.38g (35.8 mmol), 4- BROMOPHENYLBORONIC acid 7.18g (35. 8 mmol), Pd (PPh3) 4, 2. 07G (1.79 mmol), in 180ML of toluene and LOOML of ethanol was heated to obtain a clear solution. To the solution was added 30mL of 4. OM aq. NA2CO3. The reaction mixture refluxed for 4h at 80 °C. The mixture was cooled to room temperature and diluted with 300mL ethyl acetate. The organic layer was washed with 2X300ML portions of water, 2X300ML portions of sat. aq. NaCl, and dried (MGS04). After the solution was concentrated, the residue was purified by column chromatography (eluted with 7percent ETOAC-HEPTANE) to afford the desired product in 7.8g (78percent) as a white SOLID. 1H NMR (CDC13) 8.10 (d, 2H, J = 9. 0HZ), 7. 62 (d, 2H, J = 9. 0HZ), 7. 59 (d, 2H, J = 9.3Hz), 7.48 (d, 2H, J = 9.3 Hz), 3.95 (s, 3H).

Reference: [1] Patent: WO2004/99170, 2004, A2, . Location in patent: Page 57
[2] Patent: WO2006/55625, 2006, A2, . Location in patent: Page/Page column 94-95
[3] Patent: WO2006/55725, 2006, A2, . Location in patent: Page/Page column 179
[4] Patent: WO2004/99171, 2004, A2, . Location in patent: Page 116-117
  • 17
  • [ 619-44-3 ]
  • [ 1878-68-8 ]
  • [ 89901-03-1 ]
Reference: [1] ACS Catalysis, 2017, vol. 7, # 3, p. 2171 - 2175
  • 18
  • [ 288-32-4 ]
  • [ 619-44-3 ]
  • [ 101184-08-1 ]
YieldReaction ConditionsOperation in experiment
19% With (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; potassium carbonate; copper(I) bromide In N,N-dimethyl-formamide at 100℃; for 48 h; Inert atmosphere; Sealed tube For the synthesis of RK464 (Scheme 2), a round bottom flask with a magnetic stir bar was usedas a reaction vessel. To this vessel, CuBr (7.2 mg, 0.025 mmol), (1R,2R)-N1,N2-dimethyl-cyclohexane-1,2-diamine (16 L, 0.05 mmol), and imidazole (82 mg, 0.6 mmol), were added with DMF (20 mL) as asolvent. The vessel was sealed with a septum and nitrogen gas was passed through it.After reacting the initial mixture of compounds, methyl 4-iodobenzoate (262 mg, 0.5 mmol). K2CO3 (357 mg, 2.6 mmol) were added. Again, nitrogen gas was back-filled and the reaction mixturewas heated in a preheated oil bath for 48 h at constant temperature of 100 °C. Reaction progress wasregularly monitored using TLC. As the reaction progressed, the color of the mixture changed from whiteto yellow. The product was extracted using ethyl acetate and purified using flash chromatography.A pure yellow viscous product (about 40 mg) was obtained and dried under vacuum. Yield: 19percent.1H-NMR (750 MHz, CD3OD) δ: 6.75 (s, 1H, Ar-H), 6.63–6.64 (d, 2H, Ar-H), 6.19-6.20 (d, 2H, Ar-H),6.16 (s, 1H, Ar-H), 2.40 (s, 3H, CH3) (Supplementary Figure S9); HRMS (ESI) calcd C11H10N2O2 for203.0821, found 203.0808 [M+H]+, (Supplementary Figure S14). FT IR νmax cm−1: 1710.61 (carboxyl, for 203.0821, found 203.0808 [M+H]+, (Supplementary Figure S14). FT IR max cm1: 1710.61 (carboxyl,C=O), (Supplementary Figure S20). X-ray crystallography: X-ray crystallography structure for thiscompound is shown in Supplementary Figure S19 with R = 0.2.
Reference: [1] Molecules, 2016, vol. 21, # 7,
  • 19
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  • [ 1692-15-5 ]
  • [ 106047-17-0 ]
Reference: [1] Applied Organometallic Chemistry, 2019, vol. 33, # 1,
  • 20
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  • [ 160598-47-0 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 15, p. 7436 - 7444
  • 21
  • [ 619-44-3 ]
  • [ 158938-08-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3271 - 3281
  • 22
  • [ 619-44-3 ]
  • [ 113100-86-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1799 - 1802
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 16, p. 2502 - 2524
  • 23
  • [ 5419-55-6 ]
  • [ 619-44-3 ]
  • [ 99768-12-4 ]
YieldReaction ConditionsOperation in experiment
94.8% With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; In 500mL three-necked flask,Methyl 4-iodobenzoate (20.1 g, 76.7 mmol) was dissolved in dry THF (200.0 mL)Triisopropyl borate (18.0 g, 95.9 mmol) was added,Cool to -78 ° C,N-Butyllithium (6.1 g, 95.9 mmol) was added dropwise,Maintain the reaction temperature 0.5h.The reaction was completed, quenched with saturated aqueous ammonium chloride solution,1mol / L hydrochloric acid to adjust the pH to 1,Ethyl acetate (100.0 mL x 3)The combined organic phase,Saturated brine (60 mL × 1)Dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure,The residue was beaten with n-hexane, and filtered to obtain 13.1 g of 4-methoxycarbonylphenylboronic acid,Yield 94.8percent.
Reference: [1] Patent: CN106565761, 2017, A, . Location in patent: Paragraph 0023; 0024; 0079; 0080
  • 24
  • [ 688-74-4 ]
  • [ 619-44-3 ]
  • [ 99768-12-4 ]
YieldReaction ConditionsOperation in experiment
91% With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; In 500mL three-necked flask,Methyl 4-iodobenzoate (20.4 g, 77.8 mmol) was dissolved in dry THF (200.0 mL)Tri-n-butyl borate (21.5 g, 93.4 mmol) was added,Cool to -78 ° C,N-Butyllithium (5.5 g, 85.6 mmol) was added dropwise,Maintain the reaction temperature 0.5h.The reaction was completed, quenched with saturated aqueous ammonium chloride solution,1mol / L hydrochloric acid to adjust the pH to 1,Ethyl acetate (100.0 mL x 3)The combined organic phases were washed with saturated brine (60 mL × 1)Dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure,The residue was beaten with n-hexane,Filtered to give 4-methoxycarbonyl phenylboronic acid 12.7g, the yield was 91.0percent.
Reference: [1] Patent: CN106565761, 2017, A, . Location in patent: Paragraph 0039; 0040
  • 25
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  • [ 619-44-3 ]
  • [ 99768-12-4 ]
YieldReaction ConditionsOperation in experiment
94.5% With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; In 500mL three-necked flask,Methyl 4-iodobenzoate (20.3 g, 77.4 mmol) was dissolved in dry THF (200.0 mL)Trimethyl borate (16.1 g, 154.8 mmol) was added,The temperature was lowered to -78 ° C and n-butyllithium (7.4 g, 116.1 mmol) was added dropwise.Maintain the reaction temperature 0.5h.The reaction was completed, quenched with saturated aqueous ammonium chloride solution,1mol / L hydrochloric acid to adjust the pH to 1,Ethyl acetate (100.0 mL × 3), the organic phases were combined,Saturated brine (60 mL × 1), dried over anhydrous sodium sulfate,The solvent was distilled off under reduced pressure, the residue was beaten with n-hexane,The filtrate was filtered to give 4-methoxycarbonyl phenylboronic acid 13.2g, a yield of 94.5percent.
Reference: [1] Patent: CN106565761, 2017, A, . Location in patent: Paragraph 0047; 0048
  • 26
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  • [ 99768-12-4 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 2, p. 305 - 307
  • 27
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  • [ 619-44-3 ]
  • [ 99768-12-4 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
  • 28
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  • [ 249647-24-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 20, p. 4088 - 4098
  • 29
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  • [ 330792-69-3 ]
Reference: [1] Patent: WO2014/82598, 2014, A1,
[2] Patent: EP3141546, 2017, A1,
[3] Patent: CN107652294, 2018, A,
  • 30
  • [ 619-44-3 ]
  • [ 728865-23-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 8, p. 2362 - 2367
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