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Chemical Structure| 302348-51-2 Chemical Structure| 302348-51-2
Chemical Structure| 302348-51-2

4-(Hydroxymethyl)phenylboronic acid pinacol ester

CAS No.: 302348-51-2

4.5 *For Research Use Only !

Cat. No.: A151856 Purity: 98%

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Product Details of [ 302348-51-2 ]

CAS No. :302348-51-2
Formula : C13H19BO3
M.W : 234.10
SMILES Code : CC1(C)OB(OC1(C)C)C1=CC=C(CO)C=C1
MDL No. :MFCD09837617
InChI Key :GZZBZWITJNATOD-UHFFFAOYSA-N
Pubchem ID :11402050

Safety of [ 302348-51-2 ]

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

Calculated chemistry of [ 302348-51-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 17
Num. arom. heavy atoms 6
Fraction Csp3 0.54
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 69.05
TPSA ?

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

38.69 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

2.02
Log Po/w (WLOGP)?

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

1.33
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.

1.14
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

1.71
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.24

Water Solubility

Log S (ESOL):?

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

-2.69
Solubility 0.474 mg/ml ; 0.00203 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-2.46
Solubility 0.812 mg/ml ; 0.00347 mol/l
Class?

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

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

-3.83
Solubility 0.0344 mg/ml ; 0.000147 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

Yes
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

Yes
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.

-6.29 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

0.0
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)

2.86

Application In Synthesis of [ 302348-51-2 ]

* 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 [ 302348-51-2 ]

[ 302348-51-2 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 128376-64-7 ]
  • [ 302348-51-2 ]
YieldReaction ConditionsOperation in experiment
513 mg With sodium tetrahydroborate; at 20℃; for 5h; To a mixture of a4-formylbenzenboronic acid (1a, 375 mg, 2.50 mmol), pinacol (355 mg, 3.00 mmol) and anhydrous magnesium sulfate (625 mg, 5.00 mmol), methanol was added (12.50 mL). The mixture was stirred at room temperature for 6 h. After the reaction was completed, the crude solution was filtered, and then sodium borohydride (47 mg, 1.25 mmol) was added to the filtrate. Afterwards, the reaction mixture was stirred for an additional 5 h. Once the reaction was completed, the reaction mixture was filtered and the filtrate was concentrated in vacuo to give the desired product 2a as a white solid (m.p. 75?77 °C) in88percent yield (513 mg). 1H-NMR (CD3OD-d4) delta ppm 7.71 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 7.8 Hz, 2H),4.62 (s, 2H), 1.34 (s, 12H); 13C-NMR (CD3OD-d4) delta ppm 146.23, 135.93, 127.26, 85.19, 65.24, 25.34;11B-NMR (CDCl3) delta ppm 34.82.
  • 2
  • [ 302348-51-2 ]
  • [ 138500-85-3 ]
YieldReaction ConditionsOperation in experiment
94% With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 18h;Inert atmosphere; 2-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (3) The compound 2(1 eq, 5.72 mmol) was dissolved in THF (25 mL) followed by the addition of triphenylphosphine (2 eq, 11.4 mmol). The mixture was cooled to 0C with an ice bath then tetrabromomethane (2 eq, 11.4 mmol) was carefully added portion wise. The reaction was stirred at rt for 18h. The solution was poured into water (30 mL) and extracted 3 times (3 x 25 mL) with EtOAc. The combined organic extracts were dried, filtered and evaporated under vacuum. The compound was purified using column chromatography (silica gel, 99/1Hex/EtOAc) to afford the desired compound (Rf = 0.2) as a colourless solid (1.6 g, 94%). 1H-NMR (CDCI3, 600 MHz) delta 7.78 (d, J = 8.0 Hz, 2H), 7.38 (d, J = 8.0 Hz, 2H), 4.49 (s, 2H), 1.34 (s, 12H); 13C-NMR (CDC13, 150 MHz) delta 140.8, 135.3, 128.4, 84.0, 33.4, 25.0.
92% With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; at 20℃; for 4h;Cooling with ice; 4-hydroxymethylphenylboronic acid, pinacol ester (1.08 g, 4.61 mmol) was dissolved in THF (20 ml) together with triphenylphosphine (2.42 g, 9.23mmol). The reaction mixture was cooled in an ice-water bath, and carbon tetrabromide (3.06 g, 9.23 mmol) was added portion wise. After stirring for 4 hours at room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was combined and dried by sodium sulfate. After filtration, the solvent was evaporated, and the residue was purified by flash chromatography to give the product as a white solid (1.72 g, 92%). 1H NMR (300 MHz, CD2C12, delta): 7.62 (d, J = 6.0 Hz, 2H), 7.32 (d, J = 6.0 Hz, 2H), 4.58 (d, 2H), 1.34 (s, 9H); MS (ESI) m/z 297.0.
  • 3
  • [ 545-06-2 ]
  • [ 302348-51-2 ]
  • [ 911707-70-5 ]
  • 4
  • [ 302348-51-2 ]
  • C21H27BO4 [ No CAS ]
  • 5
  • [ 302348-51-2 ]
  • 2-(4-benzylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • 6
  • [ 76-09-5 ]
  • sodium-compound of pinacol [ No CAS ]
  • [ 302348-51-2 ]
  • 8
  • C19H16N2O6 [ No CAS ]
  • [ 302348-51-2 ]
  • [ 1018786-02-1 ]
  • 9
  • [ 1018781-12-8 ]
  • [ 302348-51-2 ]
  • Peroxy Lucifer 1 [ No CAS ]
  • 10
  • C28H53NO4Si3 [ No CAS ]
  • [ 302348-51-2 ]
  • C41H72BNO7Si3 [ No CAS ]
  • 11
  • C21H25NO5 [ No CAS ]
  • [ 302348-51-2 ]
  • C34H44BNO8 [ No CAS ]
  • 12
  • [ 57876-69-4 ]
  • [ 302348-51-2 ]
  • [ 1160829-14-0 ]
  • 13
  • [ 52334-81-3 ]
  • [ 302348-51-2 ]
  • [ 1160829-13-9 ]
  • 14
  • [ 302348-51-2 ]
  • [ 1169945-44-1 ]
YieldReaction ConditionsOperation in experiment
90% With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at 0 - 20℃; for 1h; To a stirred solution of <strong>[302348-51-2](4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol</strong> (1) (0.55 g, 2.35 mmol) in acetonitrile (20 mL), sodium iodide (1.1 g, 7.05 mmol) and Trimethylsilyl chloride (0.65 mL, 7.05 mmol) are added at about 0°C. The reaction mixture is allowed to stir at room temperature for about 1 hour. After completion of the reaction, solvent is evaporated under vacuum. The crude product is dissolved in saturated solution of Na2S203 to quench the unreacted iodide and the product is extracted with dichloromethane. The crude product is purified by column chromatography on silica gel using ethyl acetate\hexane (5:95) as an eluent to give product 2-(4-(iodomethyl)phenyl)-4,4,5,5-tetramethyl-l ,3,2-dioxaborolane (2) in excellent yield (90percent). 1H NMR (400 MHz, ( 7X 7 ,· ) dppm 7.73 (d, J = 8 Hz, 21 1 ). 7.37 (d, J = 8 Hz, 2H), 4.45 (s, 2H), 1.34 (s, 12H) 1 C NMR (100 MHz, ( 7 ,·) 5ppm 142.3, 135.3, 128.0, 24.9, 5.4
  • 15
  • [ 124-63-0 ]
  • [ 302348-51-2 ]
  • 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0℃; for 2h;Inert atmosphere; (ii) Synthesis of Compound (15); (4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl methanesulfonate) (see Non-patent Literature 14); Under argon atmosphere, triethylamine (3.15 mL, 22.6 mmol) and methanesulfonyl chloride (1.40 mL, 18.1 mmol) were sequentially added to a CH2Cl2 (60 mL) solution of Compound (14) (3.48 g, 14.9 mmol), and the mixture was stirred at 0 °C for 2 hours. Water (150 mL) was added to the mixture, and the mixture was extracted with CH2Cl2 (100 mL .x. 3). All the organic phases were mixed, sequentially rinsed with water (70 mL .x. 3) and a saline solution (70 mL .x. 3), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography (110 g of silica gel, n-hexane/EtOAc = 3/1) to obtain Compound (15) as a colorless solid. The Compound (15) was not purified furthermore and used in the next step. TLC 0.41 (n-hexane/EtOAc = 2/1).
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 3h;Inert atmosphere; 2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]isoindoline-1,3-dione (3a). Compound 2a (585 mg, 2.50 mmol), and dichloromethane (25.00 mL) were added to a dry flask containing a magnetic stir bar under a nitrogen atmosphere. The flask was cooled to 0 °C, then methanesulfonyl chloroide (0.29 mL, 3.75 mmol) and N,N-diisopropylethylamine (DIPEA, 0.87 mL, 5.00 mmol) were slowly added to the flask. The reaction mixture was stirred at 0 °C for 3 h. After the reaction was completed, the reaction mixture was diluted with dichloromethane (25.00 mL) before H2O (25.00 mL)was added. The organic layer was then washed with brine and dried with MgSO4. The resulting organic layer was then filtered and the filtrate was concentrated in vacuo. The resulting crude material was re-dissolved in DMF (4.68 mL) after which both potassium phthalimide salt (695 mg, 3.75 mmol), and K2CO3 (1,036 mg, 7.50 mmol) were added to the solution. The reaction was then allowed to stir at room temperature for 3 days. After the reaction was completed, the distilled H2O (20.00 mL) was slowly added to the reaction mixture to afford the formation of a solid precipitate. The reaction mixture was then filtered and the filtered cake was collected. The filtered cake was re-dissolved in tertbutanol/H2O (4:1, v/v) (10.00 mL) before a freeze-drying process was applied to remove the remaining DMF. The desired product 3a was obtained as a white solid (m.p. 166?169 °C) in 96percent yield (872 mg);1H-NMR (CDCl3) delta ppm 7.84?7.82 (m, 2 H), 7.74 (d, J = 7.85 Hz, 2 H), 7.71?7.68 (m, 2H), 7.42 (d,J = 7.85 Hz, 2H), 4.85 (s, 2H), 1.34 (s, 12H); 13C-NMR (CDCl3) delta ppm 167.90, 139.26, 135.12,133.93, 132.04, 127.76, 123.29, 83.73, 41.60, 24.77; 11B-NMR (CDCl3) delta ppm 30.94.
  • 16
  • allyl 5-amino-2-nitrobenzoate [ No CAS ]
  • [ 32315-10-9 ]
  • [ 302348-51-2 ]
  • [ 1219600-17-5 ]
  • 17
  • [ 1225050-00-9 ]
  • [ 302348-51-2 ]
  • 18
  • [ 70-34-8 ]
  • [ 302348-51-2 ]
  • [ 1225050-01-0 ]
  • 19
  • [ 1055310-43-4 ]
  • [ 302348-51-2 ]
  • [ 1219600-17-5 ]
  • 21
  • [ 7693-46-1 ]
  • [ 302348-51-2 ]
  • [ 1254765-89-3 ]
YieldReaction ConditionsOperation in experiment
80% To a solution of 4-nitrophenyl chloroformate (264 mg, 1.26 mmol) in 3 mL of DCM at 0 C was added dropwise Et3N (177 muL, 1.26 mmol). The mixture was stirred during 20 min under argon then a solution of 6a (100 mg, 0.42 mmol) in 4 mL of DCM was added dropwise to the first solution and the mixture was stirred during 3 h at r.t. The reaction was quenched with brine, extracted with DCM (3×20 mL), the organic layers were combined, dried with MgSO4 and concentrated under reduced pressure to give a crude product. The crude product was purified by column chromatography over silica gel with cyclohexane-EtOAc: 90- 10 to 60-40 to give the expected product (135 mg, yield: 80%). 1H NMR (300 MHz, CDCl3) delta 7.88-7.82 (m, 2H), 7.46-7.41 (m, 2H), 7.40-7.35 (m, 2H), 5.31 (m, 2H), 1.35 (s, 12H). 13C NMR (75 MHz, CDCl3) delta 155.47, 152.38, 145.36, 137.02, 135.15, 127.58, 127.23, 125.25, 121.74, 83.95, 70.75, 24.82. HRMS (ESI): m/z Calcd for C20H22BNO7Na, [M+Na]+:422.1387, found: 422.1367.
60% With triethylamine; In tetrahydrofuran; at 20℃; for 1h;Product distribution / selectivity; 4-(Hydroxymethyl)phenylboronic acid pinacol ester (0.5 g, 2.1 mmol) was dissolved in 20 mL of dry THF. Triethylamine (0.6 mL, 4.3 mmol) was added followed by 4-nitrophenyl chloroformate (0.47 g, 2.3 mmol) and the reaction was allowed to stir at room temperature for 1 h. The reaction was diluted with EtOAc and washed with 1.0 M HCl followed by saturated NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated. Compound B2a was purified on a silica gel column eluting with 5% EtOAc in hexanes to give 0.51 g (1.3 mmol, 60% yield) as a white solid. 1H NMR (400 MHz, CDCl3) delta=8.25 (d, J=9.2 Hz, 2H), 7.85 (d, J=8.0 Hz, 2H), 7.43 (d, J=8.0 Hz, 2H), 7.36 (d, J=9.2 Hz, 2H), 5.31 (s, 2H), 1.35 (s, 12H). 13C NMR (100 MHz, CDCl3) delta=155.7, 152.7, 145.6, 137.2, 135.4, 127.9, 125.5, 122.0, 84.2, 71.0, 25.1. ESI-MS(+): m/z 417.19 [M+NH4]+, 422.20 [M+Na]+.
In dichloromethane; at 0℃; 1) Preparation of active small molecules:Mixing 4-(hydroxymethyl)phenylboronic acid pinacol ester and p-nitrophenoxycarbonyl chloride as a molar ratio of 1:1The solution was dissolved in dichloromethane in that order, and the reaction was stirred well at 0 C.Synthesizing a small molecule capable of reversibly binding to methotrexate;
  • 22
  • [ 76-09-5 ]
  • [ 59016-93-2 ]
  • [ 302348-51-2 ]
YieldReaction ConditionsOperation in experiment
92% In tetrahydrofuran; for 22h;Reflux; A suspension of 4-(hydroxymethyl)phenylboronic acid (1.00 g, 6.6. mmol) and pinacol (0.79 g, 6.7 mmol) in tetrahydrofurane (40 mL) was refluxed over 22 h. During this time the starting materials were completely dissolved. The solvent was removed in vacuum (10 mbar), the residue redissolved in CH2Cl2 / EtOAc and purified by column chromatography on silica gel using the mixture of CH2Cl2 / EtOAc (9/1, v/v) as eluent. Yield 1.4 g (92%). Rf= 0.3 (silica, eluent - CH2Cl2 / EtOAc, 9/1, v/v). 1H NMR (200 MHz, CDCl3), delta in ppm: 1.35 (s, 12H), 4.71 (s, 2H), 7.37 (d, 2H, 3J = 8.2 Hz), 7.81 (d, 2H, 3J = 8.2 Hz).
92% In tetrahydrofuran; for 22h;Reflux; Synthesis4-(Hvdroxymethyl)phenylboronic acid pinacol ester:A suspension of 4-(hydroxymethyl)phenylboronic acid (1.00 g, 6.6 mmol) and pinacol (0.79 g, 6.7 mmol) in tetrahydrofurane (40 ml_) was refluxed over 22 h. During this time the starting materials were completely dissolved. The solvent was removed in vacuum (10 mbar), the residue redissolved in CH2CI2 / EtOAc and purified by column chromatography on silica gel using the mixture of CH2CI2 / EtOAc (9/1 , v/v) as eluent. Yield 1.4 g (92%). Rf= 0.3 (silica, eluent - CH2CI2 / EtOAc, 9/1 , v/v). H NMR (200 MHz, CDCI3), delta in ppm: 1.35 (s, 12H), 4.71 (s, 2H), 7.37 (d, 2H, 3J = 8.2 Hz), 7.81 (d, 2H, 3J = 8.2 Hz).
With magnesium sulfate; In acetonitrile; for 24h;Reflux; To a stirred solution of 4-(hydroxymethyl) phenylboronic acid (0.4 g, 2.63 mmol) in acetonitrile (15 mL), MgS04 (3 g) and pinacol (0.37 g, 3.15 mmol) are added. The reaction mixture is heated up to about 80C and allowed to reflux for about 24 hours. After completion of the reaction, solvent is evaporated under vacuum. The crude mixture is dissolved in dichloromethane and filtered. The obtained product (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl) methanol (i.e. compound 1) is used for further reaction without purification.
  • 23
  • [ 530-62-1 ]
  • [ 302348-51-2 ]
  • [ 1262015-14-4 ]
YieldReaction ConditionsOperation in experiment
85% In dichloromethane; at 20℃;Inert atmosphere; Compound 2 (660 mg, 2.82 mmol) was dissolved in 10 mL of dry CH2Cl2.Then, N,N'-carbonyldiimidazole (915 mg, 5.64 mmol) was added, and the mixture was stirred at room temperature for 1-2 h under N2. After the reaction was completed, 40 ml of CH 2 Cl 2 was added, and the mixture was washed three times with an equal amount of 1 M HCl solution, and the organic phase was dried over anhydrous sodium sulfate.Concentrated under reduced pressure to give a white solid 787mg, yield 85%.
In dichloromethane; at 20℃; for 2h; 2.07 g of 1,1'-carbonyldiimidazole and 2.07 g of 4- (hydroxymethyl) phenylboronic pinicole ester(4- (hydroxymethyl) phenylboronic acid pinacol ester) was dissolved in 20 mL of dichloromethane (DCM)And allowed to react at room temperature for 2 hours. The product was named 1 and 1 was obtained by silica gel chromatography using an eluent of 1: 1 mixture of ethyl acetate and hexane.
  • 24
  • [ 1276130-32-5 ]
  • [ 302348-51-2 ]
  • [ 1312816-01-5 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 100℃; for 3h; To a slurry of methyl 5-bromo-3-(4-methyl-benzylamino)-thiophene-2-carboxylate (154 mg, 0.45 mmol) and <strong>[302348-51-2][4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanol</strong> (158 mg, 0.68 mmol) in DMF (4.5 mL) and sat'd. aq. Na2CO3 (1.9 mL) was added Pd(PPh3)4 (73 mg). The reaction mixture was heated to 100° C. for 3 h then cooled to RT. The solvent was removed and the crude product purified by SiO2 chromatography (Isco) eluting with an EtOAc/hexane gradient (0percent to 30percent EtOAc) to afford 255 mg of methyl 5-(4-hydroxymethyl-phenyl)-3-(4-methyl-benzylamino)-thiophene-2-carboxylate (72): MS calcd for C21H21NO3S [M+H]+ 368. Found, 368.
  • 25
  • [ 1021913-05-2 ]
  • [ 302348-51-2 ]
  • C28H32BrClN2O4 [ No CAS ]
  • 26
  • [ 1314568-35-8 ]
  • [ 302348-51-2 ]
  • C26H16ClF3N2O2 [ No CAS ]
 

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Related Functional Groups of
[ 302348-51-2 ]

Organoborons

Chemical Structure| 443776-76-9

A117943 [443776-76-9]

(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

Similarity: 1.00

Chemical Structure| 253342-48-2

A145191 [253342-48-2]

4,4,5,5-Tetramethyl-2-(m-tolyl)-1,3,2-dioxaborolane

Similarity: 0.95

Chemical Structure| 195062-57-8

A196359 [195062-57-8]

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane

Similarity: 0.95

Chemical Structure| 401797-00-0

A153313 [401797-00-0]

2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.93

Chemical Structure| 195062-59-0

A184070 [195062-59-0]

4,4,5,5-Tetramethyl-2-(o-tolyl)-1,3,2-dioxaborolane

Similarity: 0.93

Aryls

Chemical Structure| 443776-76-9

A117943 [443776-76-9]

(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

Similarity: 1.00

Chemical Structure| 253342-48-2

A145191 [253342-48-2]

4,4,5,5-Tetramethyl-2-(m-tolyl)-1,3,2-dioxaborolane

Similarity: 0.95

Chemical Structure| 195062-57-8

A196359 [195062-57-8]

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane

Similarity: 0.95

Chemical Structure| 401797-00-0

A153313 [401797-00-0]

2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.93

Chemical Structure| 195062-59-0

A184070 [195062-59-0]

4,4,5,5-Tetramethyl-2-(o-tolyl)-1,3,2-dioxaborolane

Similarity: 0.93

Alcohols

Chemical Structure| 443776-76-9

A117943 [443776-76-9]

(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

Similarity: 1.00

Chemical Structure| 1400755-04-5

A129162 [1400755-04-5]

(4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

Similarity: 0.92

Chemical Structure| 651030-56-7

A138291 [651030-56-7]

2-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanol

Similarity: 0.90

Chemical Structure| 651030-55-6

A406020 [651030-55-6]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneethanol

Similarity: 0.90

Chemical Structure| 1220219-36-2

A326810 [1220219-36-2]

(1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)methanol

Similarity: 0.89