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[ CAS No. 551001-79-7 ] {[proInfo.proName]}

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Chemical Structure| 551001-79-7
Chemical Structure| 551001-79-7
Structure of 551001-79-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 551001-79-7 ]

CAS No. :551001-79-7 MDL No. :MFCD06801701
Formula : C9H9BO4 Boiling Point : -
Linear Structure Formula :- InChI Key :XLIQZZGLIJLKTF-UHFFFAOYSA-N
M.W : 191.98 Pubchem ID :22221596
Synonyms :

Calculated chemistry of [ 551001-79-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.53
TPSA : 62.83 Ų

Pharmacokinetics

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) : -6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.24
Log Po/w (WLOGP) : 0.12
Log Po/w (MLOGP) : -0.5
Log Po/w (SILICOS-IT) : -0.25
Consensus Log Po/w : 0.12

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.16
Solubility : 1.34 mg/ml ; 0.007 mol/l
Class : Soluble
Log S (Ali) : -2.16
Solubility : 1.34 mg/ml ; 0.00696 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.31
Solubility : 0.945 mg/ml ; 0.00492 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.69

Safety of [ 551001-79-7 ]

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:

Application In Synthesis of [ 551001-79-7 ]

* 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 [ 551001-79-7 ]
  • Downstream synthetic route of [ 551001-79-7 ]

[ 551001-79-7 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 13391-28-1 ]
  • [ 551001-79-7 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -30℃; for 1.5 h;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -30 - 10℃; for 2.17 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 10℃;
Step A: 5-Methoxybenzofuran (1 g, 6.8 mmol) was dissolved in tetrahydrofuran (10 ml) and cooled to -30° C. The solution was treated with n-BuLi (3.5 ml, 8.9 mmol, 2.5 M in hexanes) over 30 minutes, maintaining the internal temperature at -30° C. during the addition to give a red solution. After 1 hour at -30° C., trimethyl borate (1 ml, 8.8 mmol) was added over 10 minutes and the solution became pale brown. The resulting solution was allowed to warm slowly to 10° C. over 2 hours after which it was quenched with 6 M HCl (10 ml) and extracted with ethyl acetate (30 ml). The organics were washed with water (30 ml) and brine (30 ml) and were dried over anhydrous magnesium sulfate. After filtration, the organic solution was concentrated and the boronic acid precipitated by adding hexanes. The crystals were filtered and washed with hexanes to give an off-white solid (983 mg, 76percent): 1H NMR (500 MHz, DMSO-d6) δ 8.53 (br s, 2H), 4.47 (br d, J=8.8 Hz, 1H), 7.20 (br s, 1H), 6.94 (br dd, J=8.8, 2.5 Hz, 1H), 3.79 (br s, 3H).
37%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Inert atmosphere
Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78℃; for 0.5 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane at 20℃;
j0379j 2.5 M n-butyllithium in hexanes (2.8 mE, 7.00 mmol) was added slowly to a solution of 5-methoxy-i-benzofuran(1.0 g, 6.75 mmol) in dry tetrahydrothran (15 mL) at -78 °C under a nitrogen atmosphere. After 1 hour stirring at -78 °C, triisopropylborate (3.12 mL, 13.5 mmol) was added drop-wise and the mixture stirred for 30 minutes at -78 °C. The dry ice bath was removed, 2 M aqueous hydrochloric acid (20 mL) was added and the mixture warmed to room temperature whilst stirring overnight. The reaction mixture was poured into waler (25 mL) and extracted with diethyl ether (3 x 20 mL). The combined organics were washed with brine (20 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. Dichloromethane (20 mL) was added and the mixture sonicated for 10 minutes. The minimum amount of methanol (ca. 1 mL) was added to ffilly dissolve the solids and the solution sonicaled for 10 minutes. Heptane (20 mL) was added and the precipitated solids collected by vacuum filtration and allowed to dry under vacuum for 2 hours to give the title compound 476 mg (37percent yield) as a white solid. On NMR (500 MHz, DMSO) 8.53 (s, 2H), 7.46 (d, J= 8.94 Hz, IH), 7.39 (s, lH), 7.19 (d, J= 2.51 Hz, 1H), 6.93 (dd, J= 2.60,8.92 Hz, 1H), 3.78 (s, 3H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 6, p. 1976 - 1980
[2] Patent: US2006/52378, 2006, A1, . Location in patent: Page/Page column 96
[3] Patent: WO2016/33445, 2016, A1, . Location in patent: Paragraph 0379
  • 2
  • [ 13391-28-1 ]
  • [ 5419-55-6 ]
  • [ 551001-79-7 ]
YieldReaction ConditionsOperation in experiment
69.8%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333 h;
Stage #2: at -78 - 20℃; for 2 h;
To 5-methoxybenzofuran (188 mg, 1.269 mmol) in THF (4.0 mL) at -78 °C wasadded 1.6 N n-BuLi in hexanes (1.190 mL, 1.903 mmol) dropwise. The solution became slightly yellow. The reaction mixture was stirred at -78 °C for 20 mm, followed by addition of triisopropyl borate (0.737 mL, 3.17 mmol). After 30 mm stirring at -78 °C, the cooling bath was removed and the stirring was continued at room temperature for 1.5h. The reaction mixture was diluted with EtOAc, quenched with 3.0 mL of 1.0 N HC1.After stirring at room temperature for 25 mm, the organic layer was collected, washedwith brine and dried over sodium sulfate. After evaporation of solvent, the cmde product was dissolved in a small amount of chloroform/a drop of MeOH and charged to a 4 g silica gel cartridge which was eluted with hexanes for 2 mm., then a 10 mm gradient from 0percent to 60percent. The desired fractions were combined, concentrated and lyophilized to giveIntermediate 2A (170 mg, 0.886 mmol, 69.8 percent yield) as a white solid. ‘H NMR (500MHz, methanol-d4) ö 7.41 (d, J=9. 1 Hz, 1H), 7.30 (s, 1H), 7.14 (d, J2.5 Hz, 1H), 6.96 (dd, J=8.9, 2.6 Hz, 1H), 3.84 (s, 3H); LC-MS: method A, RT = 1.45 mm, MS (ESI) m/z: 149.0 (M-B(OH)2)t
37% With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5 h; Inert atmosphere Step 1, Method 3: (5-Methoxy-l-benzofuran-2-yl)boronic acid[0149] 2.5 M M-butyllithium in hexanes (2.8 mL, 7.00 mmol) was added slowly to a solution of 5-methoxy-l-benzofuran (1.0 g, 6.75 mmol) in dry tetrahydrofuran (15 mL) at -78 °C under a nitrogen atmosphere. After 1 hour stirring at -78 °C, triisopropylborate (3.12 mL, 13.5 mmol) was added drop-wise and the mixture stirred for 30 minutes at -78 °C. The dry ice bath was removed, 2 M aqueous hydrochloric acid (20 mL) was added and the mixture allowed to warm to room temperature whilst stirring overnight. The reaction mixture was poured into water (25 mL) and extracted with diethyl ether (3 x 20 mL). The combined organics were washed with brine (20 mL), dried over magnesium sulphate, filtered and concentrated. Dichloromethane (20 mL) was added and the mixture sonicated for 10 minutes. The minimum amount of methanol (circa 1 mL) was added to fully dissolve the solids and the solution sonicated for a 10 minutes. Heptane (20 mL) was added and the precipitated solids collected by vacuum filtration and allowed to dry under vacuum for 2 hours to give the title compound 476 mg (37percent yield) as a white solid. 5H NMR (500 MHz, DMSO) 8.53 (s, 2H), 7.46 (d, J= 8.94 Hz, 1H), 7.39 (s, 1H), 7.19 (d, J= 2.51 Hz, 1H), 6.93 (dd, J= 2.60, 8.92 Hz, 1H), 3.78 (s, 3H).
Reference: [1] Patent: WO2018/13774, 2018, A1, . Location in patent: Page/Page column 292; 397
[2] Patent: WO2016/33460, 2016, A1, . Location in patent: Paragraph 0149
[3] Journal of Biological Inorganic Chemistry, 2018, vol. 23, # 7, p. 1139 - 1151
  • 3
  • [ 13391-28-1 ]
  • [ 5419-55-6 ]
  • [ 7732-18-5 ]
  • [ 551001-79-7 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: With n-butyllithium In tetrahydrofuran at -60 - -10℃; for 1.25 h; Inert atmosphere
Stage #2: at -60 - 20℃;
Stage #3: With hydrogenchloride In tetrahydrofuran at 20℃; for 1 h;
Step 1. 5-Methoxybenzofuran-2-ylboronic acidThe solution of 5-methoxybenzofuran (1.0 g, 6.76 mmol) in dry tetrahydrofuran (50 mL) was kept below -60°C under nitrogen, while BuLi (8.10 mmol, 2.5M solution in hexane) was added dropwise. It was warmed to -10°C during 45 min and stirred at this temperature for another 30 min. The mixture was cooled again below -60°C, followed by dropwise addition of triisopropyl borate (3.8 g, 20.21 mmol). After warming to room temperature the mixture was quenched with hydrochloric acid (30 mL, 2N) and stirred for 1 h. The alkaline aqueous layer was brought to pH 5 and extracted with ethyl acetate (3 x 80 mL). All organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give 5- methoxybenzofuran-2-ylboronic acid (986 mg, 76percent), which was used for the next step without further purification.'H-NMR (300 MHz, CDC13): δ 8.52 (s, 2H), 7.45 (d, J = 9.0 Hz, 1H), 7.39 (d, J = 0.9 Hz, 1H), 7.18 (d, / = 2.7 Hz, 1H), 6.91 - 6.95 (m, 1H), 3.78 (s, 3H)
Reference: [1] Patent: WO2012/119046, 2012, A2, . Location in patent: Page/Page column 63
  • 4
  • [ 13391-28-1 ]
  • [ 688-74-4 ]
  • [ 551001-79-7 ]
YieldReaction ConditionsOperation in experiment
48%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -30℃; for 1 h;
Stage #2: at 14℃; for 12 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water
5-Methoxybenzofuran (5.3 g, 35.8 mmol) was dissolved in anhydrous THF (120 mL) and cooled to −30° C. The solution was treated with n-BuLi (18 mL, 45 mmol, 2.5 M in hexanes) over 30 min, maintaining the internal temperature at −30° C. during the addition to give a yellow solution. After 1 h at −30° C., tributyl borate (12.2 mL, 45.1 mmol) was added over 10 min and the solution became pale yellow. The resulting solution was allowed to warm slowly to 14° C. over 12 h, then was quenched with 6 M HCl (50 mL) and extracted with EtOAc (150 mL). The organics were washed with water, then brine and dried over MgSO4. After filtration, the organic solution was concentrated and the boronic acid precipitated by the addition of hexanes. The solid was filtered and washed with hexanes to give an off-white solid (3.95 g, 48percent).
Reference: [1] Patent: US2014/256936, 2014, A1, . Location in patent: Paragraph 0347
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