Home Cart Sign in  
Chemical Structure| 213318-44-6 Chemical Structure| 213318-44-6

Structure of N-Boc-indole-2-boronic acid
CAS No.: 213318-44-6

Chemical Structure| 213318-44-6

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Product Citations

Grace Trammel ; Rositha Kuniyil ; Phillip Crook ; Peng Liu ; M. Kevin Brown ;

Abstract: Indole dearomatization is an important strategy to access indolines, a motif present in a variety of natural products and pharmaceuticals. Herein, a method for transition-metal catalyzed regiodivergent dearomative arylboration of indoles to generate diverse indolines is presented. The method accomplishes intermolecular dearomatization of simple indoles through a migratory insertion pathway on substrates that lack activating or directing groups on the C2- or C3-positions. Synthetically useful C2- and C3-borylated indolines can be accessed through a simple change in N-protecting group in high regio- and diastereoselectivities (up to >50:1 rr and >20:1 dr) from readily available starting materials. Additionally, the origin of regiodivergence was explored experimentally and computationally to uncover the remarkable interplay between carbonyl orientation of the N-protecting group on indole, electronics of the C2-C3 p-bond, and sterics. The method enabled the first enantioselective synthesis of (-)-azamedicarpin.

Purchased from AmBeed:

Alternative Products

Product Details of [ 213318-44-6 ]

CAS No. :213318-44-6
Formula : C13H16BNO4
M.W : 261.08
SMILES Code : O=C(N1C(B(O)O)=CC2=C1C=CC=C2)OC(C)(C)C
MDL No. :MFCD02093045
InChI Key :SVIBPSNFXYUOFT-UHFFFAOYSA-N
Pubchem ID :2773302

Safety of [ 213318-44-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Computational Chemistry of [ 213318-44-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 9
Fraction Csp3 0.31
Num. rotatable bonds 4
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 73.97
TPSA ?

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

71.69 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

2.21
Log Po/w (WLOGP)?

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

1.1
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.

0.95
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

-0.5
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.75

Water Solubility

Log S (ESOL):?

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

-2.94
Solubility 0.301 mg/ml ; 0.00115 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.

-3.35
Solubility 0.117 mg/ml ; 0.000447 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

-2.25
Solubility 1.46 mg/ml ; 0.0056 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.

-6.32 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<0.0
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)

2.67

Application In Synthesis of [ 213318-44-6 ]

* 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 [ 213318-44-6 ]

[ 213318-44-6 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 33332-28-4 ]
  • [ 213318-44-6 ]
  • [ 1000068-28-9 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; acetonitrile; at 85℃; for 20h; [l-(tert-butoxycarbonyl)-lH-indol-2-yl]boronic acid (2.22 g, 8.49 mmol), 6- chloropyrazin-2-amine (1.00 g, 7.72 mmol), K2CO3 (2.67 g, 19.3 mmol) and Pd(PPh3)4 (180 mg, 0.15 mmol) were mixed in MeCN/water (3.5: 1) and stirred at 85 0C for 20 hours. The reaction mixture was concentrated and the residue was extracted with EtOAc (2x 40 mL) and water (50 mL). The organic layers were combined, dried (Na2SO^, filtered and concentrated to give 2.5 g of a brown solid of tert-butyl 2-(6-aminopyrazin-2-yl)- lH-indole-l-carboxylate. The material was used in the next step without further purification. To tert-butyl 2-(6-aminopyrazin-2-yl)-lH-indole- l-carboxylate (1.1 g, 3.5 mmol) in dry toluene (10 mL) were added methyl 6-chloronicotinate (0.67 g, 3.90 mmol), K2CO3 (7.35 g, 53.2 mmol), (+/-)-BINAP (0.1 1 g, 0.18 mmol) and Pd(OAc)2 (40 mg, 0.18 mmol). The mixture was re fluxed for 50 minutes. The solvent was evaporated and the residue was extracted with EtOAc (2x100 mL) and washed with water/brine (1 : 1 ; 100 mL). The organic layers were combined, dried (Na2Spsi4), filtered and concentrated to give 2 g of crude product. Purification was performed by flash chromatography (1percent NEt3 in DCM-> 1percent NEt3, 1percent MeOH in DCM). This gave tert-butyl 2-(6-[5-(methoxycarbonyl)pyridin-2- yl]amino}pyrazin-2-yl)-lH-indole- l-carboxylate (620 mg). The material was divided into four microwave tubes (155 mg, 0.35 mmol in each) and dissolved in MeOH. 2M aq NaOH (0.35 mL, 0.70 mmol) was added and the reaction mixture was irradiated in a microwave oven at 1 10 0C for 15 minutes. 6M aq HCl (0.12 mL, 0.70 mmol) was added. The reactions were combined and concen- trated in vacuo to give the crude title compound as a brown solid (720 mg). MS (ESI+) for C18H 13N5O2 m/z 332 (M+H)+.
  • 2
  • [ 22034-13-5 ]
  • [ 213318-44-6 ]
  • tert-butyl 2-(2,1,3-benzothiadiazol-4-yl)-1H-indole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 95℃; for 10h; FIG. 1 shows a synthesis reaction formula of an indolylbenzothiadiazole derivative according to Examples. N-Boc-indole-2-boronic acid (1 mmol) represented by the formula (4)4-bromo-2, 1, 3-benzothiadiazole (1 mmol) and Pd (PPh 3) 4 (0.1 mmol) represented by the formula (5)The reaction was carried out in dioxane / 2 M aqueous solution of K 2 CO 3 at 95 ° C. for 10 hours. Incidentally,"Boc" represents a tert-butoxycarbonyl group as shown by the formula (6).Next, after post-treatment according to a conventional method, purification was carried out by silica gel column chromatography to obtain a fluorescent organic dye as an indolylbenzothiadiazole derivative represented by the formula (7) in a yield of 83percent.
  • 3
  • [ 13534-90-2 ]
  • [ 213318-44-6 ]
  • C18H17BrN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In water; N,N-dimethyl-formamide; at 60℃; for 4h; A mixture of compound 1 (118 mg, 0.5 mmol), (1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid (130 mg, 0.5 mmol), aq. K3PO4 (1 M, 1.5 mmol) and Pd(dppf)Cl2 (37 mg, 0.05 mmol) in DMF (5 mL) was stirred at 60 C for 4 h. The reaction mixture was diluted with H2O and extracted with EA. The organic layer was washed with H2O, brine, dried over Na2SO4. After concentrated, the residue was purified by prep-TLC (PE : EA = 5:1) to give the product of compound 2 (100 mg, yield: 54 %). 1H NMR (CDCl3, 400 MHz) delta 8.77 (s, 1H), 8.58 (d, J = 4.4Hz, 1H), 8.30 (d, J = 8.4Hz, 1H), 7.60 (d, J = 7.6Hz, 1H), 7.25~7.41 (m, 3H), 6.58 (s, 1H), 1.33 (s, 9H).
  • 4
  • [ 84539-22-0 ]
  • [ 213318-44-6 ]
  • t-butyl 2-(2-morpholinopyrimidin-5-yl)-1H-indole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
A 1 dram vial was charged with aryl bromide (122 mg, 0.5 mmol), aryl boronic acid (196 mg, 0.75 mmol) and K3PO4 (172 mg, 0.75 mmol). 2 wt % TPGS is added to the vial (1 mL) and the mixture is set to stir for about 5 min. The catalyst solution is added to the reaction mixture (0.25 mL, 0.5 mol % Pd) and the reaction vessel is purged with argon, sealed with Teflon and set to stir for 1.5 hrs at 45 C.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 213318-44-6 ]

Organoborons

Chemical Structure| 913388-66-6

A100229 [913388-66-6]

(1-(tert-Butoxycarbonyl)-5-((tert-butoxycarbonyl)amino)-1H-indol-2-yl)boronic acid

Similarity: 1.00

Chemical Structure| 1217500-59-8

A134746 [1217500-59-8]

(6-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid

Similarity: 0.90

Chemical Structure| 1072944-96-7

A244499 [1072944-96-7]

tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

Similarity: 0.87

Chemical Structure| 1310384-28-1

A197107 [1310384-28-1]

(1-(tert-Butoxycarbonyl)-5,6-dichloro-1H-indol-2-yl)boronic acid

Similarity: 0.86

Chemical Structure| 1000068-25-6

A101983 [1000068-25-6]

(1-(tert-Butoxycarbonyl)-4-fluoro-1H-indol-2-yl)boronic acid

Similarity: 0.85

Amides

Chemical Structure| 913388-66-6

A100229 [913388-66-6]

(1-(tert-Butoxycarbonyl)-5-((tert-butoxycarbonyl)amino)-1H-indol-2-yl)boronic acid

Similarity: 1.00

Chemical Structure| 1217500-59-8

A134746 [1217500-59-8]

(6-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid

Similarity: 0.90

Chemical Structure| 1072944-96-7

A244499 [1072944-96-7]

tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

Similarity: 0.87

Chemical Structure| 1310384-28-1

A197107 [1310384-28-1]

(1-(tert-Butoxycarbonyl)-5,6-dichloro-1H-indol-2-yl)boronic acid

Similarity: 0.86

Chemical Structure| 1000068-25-6

A101983 [1000068-25-6]

(1-(tert-Butoxycarbonyl)-4-fluoro-1H-indol-2-yl)boronic acid

Similarity: 0.85

Related Parent Nucleus of
[ 213318-44-6 ]

Indoles

Chemical Structure| 913388-66-6

A100229 [913388-66-6]

(1-(tert-Butoxycarbonyl)-5-((tert-butoxycarbonyl)amino)-1H-indol-2-yl)boronic acid

Similarity: 1.00

Chemical Structure| 1217500-59-8

A134746 [1217500-59-8]

(6-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid

Similarity: 0.90

Chemical Structure| 1072944-96-7

A244499 [1072944-96-7]

tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

Similarity: 0.87

Chemical Structure| 1310384-28-1

A197107 [1310384-28-1]

(1-(tert-Butoxycarbonyl)-5,6-dichloro-1H-indol-2-yl)boronic acid

Similarity: 0.86

Chemical Structure| 1000068-25-6

A101983 [1000068-25-6]

(1-(tert-Butoxycarbonyl)-4-fluoro-1H-indol-2-yl)boronic acid

Similarity: 0.85