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Chemical Structure| 55552-70-0 Chemical Structure| 55552-70-0

Structure of 3-Furanboronic acid
CAS No.: 55552-70-0

Chemical Structure| 55552-70-0

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Product Details of [ 55552-70-0 ]

CAS No. :55552-70-0
Formula : C4H5BO3
M.W : 111.89
SMILES Code : OB(C1=COC=C1)O
MDL No. :MFCD01319007
InChI Key :CYEFKCRAAGLNHW-UHFFFAOYSA-N
Pubchem ID :2734358

Safety of [ 55552-70-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 55552-70-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 5
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 28.53
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

53.6 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.11
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-1.04
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-1.76
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.17
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.81

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.86
Solubility 15.4 mg/ml ; 0.138 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.56
Solubility 30.6 mg/ml ; 0.274 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.44
Solubility 40.5 mg/ml ; 0.362 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.06 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.73

Application In Synthesis of [ 55552-70-0 ]

* 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 [ 55552-70-0 ]

[ 55552-70-0 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 55552-70-0 ]
  • [ 53848-17-2 ]
  • 2-furan-3-yl-6-methyl-phenylamine [ No CAS ]
  • 2
  • [ 55552-70-0 ]
  • [ 32138-69-5 ]
  • [ 167948-78-9 ]
  • 3
  • [ 72287-26-4 ]
  • [ 317830-16-3 ]
  • [ 55552-70-0 ]
  • [ 317826-94-1 ]
YieldReaction ConditionsOperation in experiment
2-[1-(3-Nitrophenyl)ethylamino]-4-[benzimidazol-1-yl]-6-(furan-3-yl)pyrimidine The title compound was prepared from 2-[1-(3-nitrophenyl)ethylamino]-4-[benzimidazol-1-yl]-6-chloropyrimidine and furan-3-boronic acid according to the precedure described in EXAMPLE 306, Step C and using [1,1'-bis(diphenylphosphino)ferrocene]-dichloropalladium(H) as catalyst. Mass spectrum (CH3CN/TFA/NH4O2CH/ESI) 427.0 (M+1).
  • 4
  • [ 55552-70-0 ]
  • [ 1151665-15-4 ]
  • [ 1151665-16-5 ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.333333h;Inert atmosphere; Microwave irradiation; (step 2) To a mixed solution of the compound (0.300 g) obtained in step 1, 3-furylboronic acid (0.187 g) and potassium carbonate (0.154 g) in DME/water (6 mL)/0.6 mL) was added under an argon atmosphere tetrakis(triphenylphosphine)palladium (0) (Pd(PPh3)4) (0.129 g), and the reaction vessel was irradiated in a microwave reaction apparatus at 150C for 20 min. To the reaction solution was added water, and the resulting product was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (solvent gradient: 0?30% ethyl acetate/hexane) to give tert-butyl 2-(3-furyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (0.310 g, 92%) as an oil. 1H-NMR(CDCl3):delta1.50(9H,s), 2.95-3.05(2H,m), 3.73-3.77(2H,m), 4.58(2H,s), 6.87(1H,dd,J=1.7Hz,0.7Hz), 7.29(1H,d,J=8.2Hz), 7.39(1H,d,J=8.2Hz), 7.47(1H,dd,J=1.7Hz,1.7Hz), 7.99(1H,s)
  • 5
  • [ 1445-39-2 ]
  • [ 55552-70-0 ]
  • [ 1111101-87-1 ]
  • 6
  • [ 55552-70-0 ]
  • [ 100189-84-2 ]
  • [ 1458655-31-6 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere; Step 1: 3-(4-Bromo-3,5-dimethylphenyl)furan A mixture of <strong>[100189-84-2]2,5-dibromo-1,3-dimethylbenzene</strong> (2.00 g), 1-furan-3-ylboronic acid (856 mg), and 2 M aqueous Na2CO3 solution (11 mL) in 1,4-dioxane (40 mL) is purged with argon for 5 min. Tetrakis-triphenylphosphine-palladium-(0) (270 mg) is added and the mixture is stirred at 100 C. over night. More tetrakis-triphenylphosphine-palladium-(0) (50 mg) is added and the mixture is stirred for another 5 h at 100 C. After cooling to room temperature the mixture is diluted with ethyl acetate and aqueous NH4Cl solution. The aqueous phase is extracted with ethyl acetate and the combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0?90:10) to give the title compound. LC (method 7): tR=1.22 min; Mass spectrum (EI+): m/z=250 [M]+.
  • 7
  • [ 676448-17-2 ]
  • [ 55552-70-0 ]
  • tert-butyl 4-(furan-3-yl)-1H-indole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.8% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; at 80℃; for 6h;Inert atmosphere; A solution of fert-butyl 4-bromo-lH-indole-l-carboxylate (LXXI) (10 g, 33.8 mmol), 3-furylboronic acid (LXXII) (5.29 g, 47.3 mmol), K3P04 (14.3 g, 67.5 mmol) and Pd(dppf)Cl2 (1.24 g, 1.69 mmol) in dioxane (150 mL) was heated to 80C for 6 hours under N2. The mixture was filtered and the filtrate was concentrated, the residue was purified by MPLC (PE:EtOAc = 10: 1) to give fert-butyl 4-(furan-3-yl)-lH-indole-l-carboxylate (LXXIII) (8.4 g, 29.6 mmol, 87.8% yield) as yellow oil. NMR (CDC13, 400 MHz) delta ppm 1.70 (s, 9H), 6.7 - 6.81 (m, 2H), 7.28 - 7.38 (m, 2H), 7.56 (d, J=1.6Hz, 1H), 7.66 (d, J=4Hz, 1H), 7.79 (s, 1H), 8.13 (d, J=8Hz, 1H); ESIMS found for Ci7Hi7N03 mlz 284.1 (M+H).
87.8% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; at 80℃; for 6h;Inert atmosphere; A solution of fert-butyl 4-bromo-lH-indole-l-carboxylate (LXXXVIII) (10 g, 33.8 mmol), 3-furylboronic acid (LXXXIX) (5.29 g, 47.3 mmol), K3P04 (14.3 g, 67.5 mmol) and Pd(dppf)Cl2 (1.24 g, 1.69 mmol) in dioxane (150 mL) was heated to 80C for 6 h under N2. The mixture was filtered and the filtrate was concentrated, the residue was purified by MPLC (PE:EtOAc = 10: 1) to give fert-butyl 4-(furan-3-yl)-lH-indole-l-carboxylate (XC) (8.4 g, 29.6 mmol, 87.8% yield) as yellow oil. NMR (CDC13, 400 MHz) delta ppm 1.70 (s, 9H), 6.7 - 6.81 (m, 2H), 7.28 - 7.38 (m, 2H), 7.56 (d, J=1.6Hz, 1H), 7.66 (d, J=4Hz, 1H), 7.79 (s, 1H), 8.13 (d, J=8Hz, 1H); ESIMS found for Ci7Hi7N03 mlz 284.1 (M+H).
87.8% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; at 80℃; for 6h;Inert atmosphere; A solution of <strong>[676448-17-2]tert-butyl 4-bromo-1H-indole-1-carboxylate</strong> (LXXI) (10 g, 33.8 mmol), 3-furylboronic acid (LXXII) (5.29 g, 47.3 mmol), K3PO4 (14.3 g, 67.5 mmol) and Pd(dppf)Cl2 (1.24 g, 1.69 mmol) in dioxane (150 mL) was heated to 80C for 6 h under N2. The mixture was filtered and the filtrate was concentrated, the residue was purified by MPLC (PE:EtOAc = 10: 1) to give tert-butyl 4-(furan-3-yl)-1H-indole-1-carboxylate (LXXIII) (8.4 g, 29.6 mmol, 87.8% yield) as yellow oil. 1H NMR (CDCI3, 400 MHz) delta ppm 1.70 (s, 9H), 6.7 - 6.81 (m, 2H), 7.28 - 7.38 (m, 2H), 7.56 (d, J=1.6Hz, 1H), 7.66 (d, J=4Hz, 1H), 7.79 (s, 1H), 8.13 (d, J=8Hz, 1H); ESIMS found for C17H17NO3 m/z 284.1 (M+H).
87.8% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; at 80℃; for 6h;Inert atmosphere; A solution of <strong>[676448-17-2]tert-butyl 4-bromo-1H-indole-1-carboxylate</strong> (LXXI) (10 g, 33.8 mmol), 3-furylboronic acid (LXXII) (5.29 g, 47.3 mmol), K3P04 (14.3 g, 67.5 mmol) and Pd(dppf)C12 (1.24 g, 1.69 mmol) in dioxane (150 mL) was heated to 80C for 6 h under N2. The mixture was filtered and the filtrate was concentrated, the residue was purified by MPLC (PE:EtOAc = 10:1) to give tert-butyl 4-(furan-3-yl)-1H-indole-1-carboxylate (LXXIII) (8.4 g, 29.6 mmol, 87.8% yield) as yellow oil. ?H NMR (CDC13, 400 MHz) ppm 1.70 (s, 9H), 6.7 - 6.81 (m, 2H), 7.28-7.38 (m, 2H), 7.56 (d,J1.6Hz, 1H), 7.66 (d,J=4Hz, 1H), 7.79 (s, 1H), 8.13 (d,J=8Hz, 1H); ESIMS found for C,7H,7N03 mlz 284.1 (M+H).

  • 8
  • [ 55552-70-0 ]
  • [ 1234616-70-6 ]
  • C15H8ClN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 110.0℃; for 3.0h; General procedure: To an argon degassed solution of 6-halogeno-2,4-dichloropyrido[2,3-d]pyrimidine 6 or 7 (0.5 mmol) in toluene (6mL) the desired (Het)aryl boronic acid was added then (1.5 equiv)potassium carbonate and (0.05 equiv) Pd(PPh3)4 were also added.The reaction was stirred at 110C for the desired time. After completion of the reaction, 10 mL of water was added, and then extracted with dichloromethane (3 10 mL), the organic layers were combined and dried using magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained material was purified on silica gel by column chromatography (CH2Cl2/PE: 90/10)to afford compounds 8-12. 2,4-Dichloro-6-(4-methoxyphenyl)pyrido[2,3-d]pyrimidine (8) (C14H9Cl2N3O): Compound 8 was obtained from 2,4,6-trichloropyrido[2,3-d]pyrimidine 6 using 4-methoxyphenyl boronic acid (1.05 equiv), as a white solid in 83%yield.
 

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