114527-28-5|4-(4'-Methyl-[2,2'-bipyridin]-4-yl)butanoic acid| Ambeed

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Quality Control of [ 114527-28-5 ] Purity: 98% SDS Specification

COA

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NMR

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Product Details of [ 114527-28-5 ]

CAS No. :	114527-28-5
Formula :	C₁₅H₁₆N₂O₂
M.W :	256.30
SMILES Code :	O=C(O)CCCC1=CC(C2=NC=CC(C)=C2)=NC=C1
MDL No. :	MFCD15144908
InChI Key :	LFMPLEMXVCGLMX-UHFFFAOYSA-N
Pubchem ID :	14381089

Safety of [ 114527-28-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 114527-28-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	19
Num. arom. heavy atoms	12
Fraction Csp3	0.27
Num. rotatable bonds	5
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	73.59
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	63.08 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.28
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.96
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.86
Log P_o/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.	1.28
Log P_o/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	3.4
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.35

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.8
Solubility	0.405 mg/ml ; 0.00158 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.	-2.91
Solubility	0.315 mg/ml ; 0.00123 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	-5.15
Solubility	0.00182 mg/ml ; 0.0000071 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	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	Yes
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.	-6.47 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.	0.56

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	0.0 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)	2.24

Application In Synthesis of [ 114527-28-5 ]

* 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 [ 114527-28-5 ]

[ 114527-28-5 ] Synthesis Path-Downstream 1~35

1
[ 6066-82-6 ]
[ 114527-28-5 ]
[ 130699-88-6 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 5654 - 5655.
[2]Journal of the American Chemical Society,1991,vol. 113,p. 283 - 291.

2
[ 100-02-7 ]
[ 114527-28-5 ]
[ 130699-87-5 ]

References: [1]Journal of the American Chemical Society,1991,vol. 113,p. 283 - 291.

3
[ 114527-28-5 ]
[ 115373-31-4 ]

References: [1]Monatshefte fur Chemie,1988,vol. 119,p. 1 - 16.

4
[ 115008-01-0 ]
[ 114527-28-5 ]

References: [1]Journal of Organic Chemistry,1989,vol. 54,p. 1731 - 1735.

5
[ 114527-27-4 ]
[ 114527-28-5 ]

References: [1]Monatshefte fur Chemie,1988,vol. 119,p. 1 - 16.

6
[ 114527-28-5 ]
N-(2-[2-(2-aminoethoxy)-ethoxy]-ethyl)-4-(4'-methyl-[2,2']bipyridin-4-yl)-butyramide [ No CAS ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 5654 - 5655.

7
[ 1134-35-6 ]
[ 114527-28-5 ]

References: [1]Monatshefte fur Chemie,1988,vol. 119,p. 1 - 16.
[2]Journal of Organic Chemistry,1989,vol. 54,p. 1731 - 1735.

8
[ 114527-28-5 ]
[ 114527-29-6 ]

References: [1]Monatshefte fur Chemie,1988,vol. 119,p. 1 - 16.

9
[ 114549-79-0 ]
[ 114527-28-5 ]

References: [1]Monatshefte fur Chemie,1988,vol. 119,p. 1 - 16.

10
[ 104704-11-2 ]
[ 114527-28-5 ]

References: [1]Monatshefte fur Chemie,1988,vol. 119,p. 1 - 16.

11
[ 115008-00-9 ]
[ 114527-28-5 ]

References: [1]Journal of Organic Chemistry,1989,vol. 54,p. 1731 - 1735.

12
[ 114527-28-5 ]
[ 130699-90-0 ]

References: [1]Journal of the American Chemical Society,1991,vol. 113,p. 283 - 291.

13
[ 114527-28-5 ]
[ 130699-89-7 ]

References: [1]Journal of the American Chemical Society,1991,vol. 113,p. 283 - 291.

14
cis-bis-(2,2′-bipyridine) dichlororuthenium(II) dihydrate [ No CAS ]
[ 114527-28-5 ]
Ru(bipy)2{bipy(CH₃)(C₃H₆COOHN)}Cl₂*3H₂O [ No CAS ]

References: [1]Monatshefte fur Chemie,1988,vol. 119,p. 1 - 16.

15
tetrakis(2-phenyl-4-methylpyridinato-N,C(2'))bis(μ-chloro)diiridium(III) [ No CAS ]
[ 114527-28-5 ]
[ 1360816-41-6 ]

References: [1]Dalton Transactions,2012,vol. 41,p. 2582 - 2591.

16
[(Ir(NC₅H₄C₆H₃CH₂OCH₂C₆H₃(N(C₆H₄)2)2)2Cl)2] [ No CAS ]
[ 114527-28-5 ]
[ 1360816-45-0 ]

References: [1]Dalton Transactions,2012,vol. 41,p. 2582 - 2591.

17
[(Ir(C₆H₄C₅H₃(CH₂OCH₂C₆H₃(N(C₆H₄)2)2)N)2Cl)2] [ No CAS ]
[ 114527-28-5 ]
[ 1360816-42-7 ]

References: [1]Dalton Transactions,2012,vol. 41,p. 2582 - 2591.

18
4C₆H₄C₅H₃(CH₂OCH₂C₆H₃(OCH₂C₆H₃(N(C₆H₄)2)2)2)N^(1-)*2Ir⁽³⁺⁾*2Cl^(1-)=[(C₆H₄C₅H₃(CH₂OCH₂C₆H₃(OCH₂C₆H₃(N(C₆H₄)2)2)2)N)2IrCl]2 [ No CAS ]
[ 114527-28-5 ]
2C₆H₄C₅H₃(CH₂OCH₂C₆H₃(OCH₂C₆H₃(N(C₆H₄)2)2)2)N^(1-)*Ir⁽³⁺⁾*CH₃(NC₅H₃)2C₃H₆CO₂H*Cl^(1-)=C₁₇₇H₁₂₈IrN₁₂O₈Cl [ No CAS ]

References: [1]Dalton Transactions,2012,vol. 41,p. 2582 - 2591.

19
4C₆H₄C₅H₃(CH₂OCH₂C₆H₃(OCH₂C₆H₃(OCH₂C₆H₃(N(C₆H₄)2)2)2)2)N^(1-)*2Ir⁽³⁺⁾*2Cl^(1-)=[(C₁₅₇H₁₀₈N₉O₇)2IrCl]2 [ No CAS ]
[ 114527-28-5 ]
2C₆H₄C₅H₃(CH₂OCH₂C₆H₃(OCH₂C₆H₃(OCH₂C₆H₃(N(C₆H₄)2)2)2)2)N^(1-)*Ir⁽³⁺⁾*CH₃(NC₅H₃)2C₃H₆CO₂H*Cl^(1-)=C₃₂₉H₂₃₂ClIrN₂₀O₁₆ [ No CAS ]

References: [1]Dalton Transactions,2012,vol. 41,p. 2582 - 2591.

20
[{Ir(μ-Cl)(2-(p-tolyl)pyridinato)₂}₂] [ No CAS ]
[ 114527-28-5 ]
[ 1360816-44-9 ]

References: [1]Dalton Transactions,2012,vol. 41,p. 2582 - 2591.

21
tetrakis(6-(2-benzothienyl)phenanthridine)(μ-dichloro)diiridium(III) [ No CAS ]
[ 114527-28-5 ]
[(6-(benzo[b]thiophen-2-yl)phenanthridine)₂Ir(4-(4′-methyl-[2,2′-bipyridin]-4-yl)butanoic acid)]Cl [ No CAS ]

References: [1]Dalton Transactions,2014,vol. 43,p. 16872 - 16879.
[2]Dalton Transactions,2017,vol. 46,p. 355 - 363.

22
[ 1134-35-6 ]
[ 2417-90-5 ]
[ 114527-28-5 ]

References: [1]Dalton Transactions,2014,vol. 43,p. 16872 - 16879.

23
[Ir₂(2-phenylbenzothiazole(-1H))4Cl₂] [ No CAS ]
[ 114527-28-5 ]
[(2-phenylbenzo[d]thiazole)₂Ir(4-(4′-methyl-[2,2′-bipyridin]-4-yl)butanoic acid)]Cl [ No CAS ]

References: [1]Dalton Transactions,2014,vol. 43,p. 16872 - 16879.
[2]Dalton Transactions,2017,vol. 46,p. 355 - 363.

24
[(6-phenylphenanthridine)₂IrCl]₂ [ No CAS ]
[ 114527-28-5 ]
Ir(6-phenylphenanthridine)2 carboxypropylphenyl-bipyridine chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	In 2-ethoxy-ethanol;Reflux; Inert atmosphere;	Example 3 Synthesis of Ir(6-phenylphenanthridine)2 carboxypropylphenyl-bipyridine complex as chloride salt [0236] [0237] A mixture of dimer [(6-phenylphenanthridine)2IrCl]2 (163 mg, 0.110 mmol), 4-(4-methyl-2,2-bipyridine-4?-yl)-butyric acid (60 mg, 0.232 mmol) in 2-ethoxyethanol (15 ml) was heated at reflux under nitrogen atmosphere overnight. The product was precipitated with water and filtered off. The residue was washed with Et2O. The complex has a Rf=0.57 in a TLC (dichlorometane/MeOH 10:1). The product was purified by chromatography column (silica) using dichloromethane/MeOH (gradient 10:1 to 5:1). Yield: 25% NMR: [0238] 1H NMR (300 MHz, DMSO-d6) delta 9.22-89.17 (t, J=6.0 Hz, 2H), 8.86-8.80 (t, J=9.0 Hz, 2H), 8.66-8.60 (t, J=6.0 Hz, 2H), 8.53-8.48 (m, 2H), 8.40-8.38 (m, 2H), 8.11-7.99 (m, 6H), 7.62-7.59 (d, J=9.0 Hz, 2H), 7.52-7.46 (t, J=9.0 Hz, 2H), 7.38-7.34 (t, J=6.0 Hz, 2H), 7.29-7.24 (t, J=9.0 Hz, 2H), 7.13-7.09 (m, 2H), 6.90-6.85 (m, 2H), 6.90-6.85 (m, 2H), 6.88-6.75 (t, J=9.0 Hz, 2H), 2.21-2.17 (m, 2H), 1.83-1.77 (m, 2H), 1.55-1.42 (m, 2H). MS [ESI-MS(+)]: [0239] [M]+ calc 957.27936. found 957.27754

References: [1]Patent: US2015/147751,2015,A1 .Location in patent: Paragraph 0236-0239.

25
[Ru(dipyrido[3,2-a:2’,3’-c]phenazine)(dmb"-{CO₂CH₃}₂)]Cl₂ [ No CAS ]
[ 114527-28-5 ]
[Ru(dipyrido[3,2-a:2’,3’-c]phenazine)(dmb’’-{CO₂CH₃}₂)(dmb’-CO₂^-)]Cl [ No CAS ]

References: [1]Chemistry - A European Journal,2015,vol. 21,p. 10983 - 10987.

26
ruthenium trichloride [ No CAS ]
[ 114527-28-5 ]
C₄₅H₄₈N₆O₆Ru [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 12h;Reflux;	Synthesis of a weak light frequency upconversion triplet sensitizer4 - methyl - 4 - butyric acid - 2,2 - bipyridine and ruthenium trichloride were added to ethylene glycol ether solvent, and the reaction was heated at refluxAfter 12 hours, the solvent was removed and recrystallization was carried out to give tris (4-methyl-4-butyldicarboxylic acid 2,2-bipyridyl)ruthenium complex.

References: [1]Patent: CN105601560,2016,A .Location in patent: Paragraph 0020; 0021.

27
(dmpq)2Ir2Cl2(dmpq)2 [ No CAS ]
[ 114527-28-5 ]
[(2-(3,5-dimethylphenyl)quinoline)₂Ir(4-(4′-methyl-[2,2′-bipyridin]-4-yl)butanoic acid)]Cl [ No CAS ]

References: [1]Dalton Transactions,2017,vol. 46,p. 355 - 363.

28
cis-bis-(2,2′-bipyridine) dichlororuthenium(II) dihydrate [ No CAS ]
[ 114527-28-5 ]
Ru(2,2’-bipyridine)₂(4-methyl-4’carboxypropyl-2,2’-bipyridine)Cl₂ [ No CAS ]

References: [1]Dalton Transactions,2017,vol. 46,p. 355 - 363.

29
[iridium(III)(μ-chloro)(2-phenylpyridine)2]2 [ No CAS ]
[ 114527-28-5 ]
[(2-phenylpyridine)₂Ir(4-(4′-methyl-[2,2′-bipyridin]-4-yl)butanoic acid)]Cl [ No CAS ]

References: [1]Dalton Transactions,2017,vol. 46,p. 355 - 363.

30
bis[2-(2,4-difluorophenyl)pyridinato-N,C₆']iridium(III) chloride dimer [ No CAS ]
[ 114527-28-5 ]
[(2-(2,4-difluorophenyl)pyridine)₂Ir(4-(4′-methyl-[2,2′-bipyridin]-4-yl)butanoic acid)]Cl [ No CAS ]

References: [1]Dalton Transactions,2017,vol. 46,p. 355 - 363.

31
sodium hexaflorophosphate [ No CAS ]
ruthenium(dipyridophenazine)(4,4’-dimethyl-2,2’-bipyridine-(CO₂CH₃)₂Cl₂) [ No CAS ]
[ 114527-28-5 ]
C₅₃H₄₉N₈O₆Ru⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: Prepared from 15 mg scale reactions with the Ru(dppz)(bpy?-CO2CH3)2Cl2 complex described above. The bis-ligated starting material was massed dry on paper and transferred to a 10 mL schlenck bulb flask along with one equivalent of bpy?-CO2CH3 (Complex 7) or bpy?-CO2H (Complex 8), both transferred as oils. Reactions involved refluxing approximately 4 mL 1:1 ethanol:water for 36-48 h with vigorous stilling under the protection of nitrogen and in low light conditions. The work up for these reactions followed general procedures. (73% yield for Complex 7; 85% yield for Complex 8)

References: [1]Patent: US9969759,2018,B2 .Location in patent: Page/Page column 14.

32
sodium hexaflorophosphate [ No CAS ]
ruthenium(dipyridophenazine)((4-methyl-4’-butyric acid methyl ester-2,2’-bipyridyl)Cl₂) [ No CAS ]
[ 114527-28-5 ]
C₄₉H₄₃N₈O₄Ru⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		General procedure: Prepared from 15 mg scale reactions with the Ru(dppz)(bpy?-CO2CH3)Cl2 complex described above. The bis-ligated starting material was massed dry on paper and transferred to a 10 mL schlenck bulb flask along with one equivalent of 4,4?-dimethyl-2,2?-bipyridine (Complex 2), bpy?-CO2H transferred as an oil (Complex 5), or bpy?-(CO2H)2 (Complex 9). Reactions involved refluxing approximately 4 mL 1:1 ethanol:water for 36-48 h with vigorous stilling under the protection of nitrogen and in low light conditions. The work up for these reactions followed general procedures. (87% yield for Complex 2; 77% yield for Complex 5; 72% yield for Complex 9). Complexes were isolated from their filtered aqueous reaction mixtures by precipitating them with aqueous solutions containing approximately 30 equivalents of sodium hexafluorophosphate and collecting the resulting brightly-colored orange-red solids on a fine-porosity 60 mL fine glass frit. The complexes were subsequently washed 2×5-10 cm2 deionized water, 3× full portions diethyl ether, and dried via suction. Characterization of the complexes was typically performed on filtered acetone solutions and the respective chloride salts were re-obtained through precipitation by 10 equivalents of tetrabutylammonium chloride, also dissolved in acetone. These suspensions were centrifuged and washed 2×1 cm2 acetone, using 10,500 rpm spin-down conditions at 4 degrees Celsius for 30-40 minutes. The chloride salts were dried under vacuum before redissolving in water for photophysical characterization.

References: [1]Patent: US9969759,2018,B2 .Location in patent: Page/Page column 13.

33
[ 114527-28-5 ]
C₃₇H₃₂IrN₄O₂⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

References: [1]Nucleosides, nucleotides and nucleic acids,2020,vol. 39,p. 69 - 81.
[2]Nucleosides, nucleotides and nucleic acids,2020,vol. 39,p. 69 - 81.

34
[ 114527-28-5 ]
C₄₁H₃₅IrN₅O₄⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

References: [1]Nucleosides, nucleotides and nucleic acids,2020,vol. 39,p. 69 - 81.
[2]Nucleosides, nucleotides and nucleic acids,2020,vol. 39,p. 69 - 81.
[3]Nucleosides, nucleotides and nucleic acids,2020,vol. 39,p. 69 - 81.

35
ammonium hexafluorophosphate [ No CAS ]
[iridium(III)(μ-chloro)(2-phenylpyridine)2]2 [ No CAS ]
[ 114527-28-5 ]
[ 107-21-1 ]
C₃₇H₃₂IrN₄O₂⁽¹⁺⁾*F₆P^(1-) [ No CAS ]
C₃₉H₃₆IrN₄O₃⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%; 38%		A mixture of [Ir(ppy)2Cl]2 (182.3 mg, 0.17 mmol) and <strong>[114527-28-5]4-[4'-methyl-(2,2'-bipyridin)-4-yl]butanoic acid</strong> (96.0 mg, 0.38 mmol) in ethylene glycol (8 mL) was stirred at 150 C for 19 hours. After cooling to room temperature,150 mL of H2O was added. The mixture was washed with Et2O, andthe aqueous layer was heated to 65 C. NH4PF6 (851 mg, 5.22 mmol) in 8mL of H2O was added, and the yellow precipitate was formed. After cooling the suspension to 0 C, the yellow solid was separated through filtration. The crude residue was purified by column chromatography(CHCl3/MeOH = 100:1 to 5:1) to give compound 2 (144.4 mg, 47%) and 3 (121.8 mg, 38%) as a yellow solid, respectively. Compound 2. 1H NMR (500 MHz, CDCl3): delta 8.50 (s, 1H), 8.49 (s, 1H),7.89 (d, J=8.0 Hz, 1 H), 7.88 (d, J=8.0 Hz, 1 H), 7.78-7.73 (m, 4 H), 7.66(d, J=7.0 Hz, 2 H), 7.51 (d, J=6.0 Hz, 2 H), 7.21 (d, J=4.5 Hz, 1 H), 7.16(d, J=5.5 Hz, 1 H), 7.05-6.98 (m, 4 H), 6.91-6.87 (m, 2 H), 6.29 (d,J=7.5 Hz, 2 H), 2.90 (dd, J=8.0, 7.5 Hz, 2 H), 2.58 (s, 3H), 2.45 (dd,J=7.5, 6.5 Hz, 2 H), 2.06-2.00 (m, 2 H). 13C NMR (100 MHz, CDCl3): delta 178.0, 167.7, 167.7, 155.7, 155.3, 155.3, 152.3, 150.6, 150.6, 149.8, 149.4,148.6, 148.5, 138.0, 138.0, 131.7, 130.7, 130.6, 130.6, 128.8, 128.0, 125.9,125.2, 124.7, 124.6, 123.4, 123.3, 122.4, 122.4, 119.5, 119.5, 34.2, 33.0, 24.8,21.3. IR (ATR) cm-1: 3041, 2924, 2854, 1707, 1608, 1583, 1478, 1421.HRMS (ESI-TOF): calcd for C37H32IrN4O2 [M-PF6]+ 757.2154,found 757.2153. Compound 3. 1H NMR (500 MHz, CDCl3): delta 8.54 (s, 1H), 8.54 (s, 1H),7.90 (d, J=8.0 Hz, 1 H), 7.90 (d, J=8.0 Hz, 1 H), 7.78-7.73 (m, 4 H), 7.67(d, J=8.0 Hz, 2 H), 7.54-7.51 (m, 2 H), 7.20 (d, J=5.5 Hz, 1 H), 7.16 (d,J=5.5 Hz, 1 H), 7.05-7.01 (m, 4 H), 6.90 (t, J=7.5 Hz, 2 H), 6.30 (d,J=7.5 Hz, 1 H), 6.29 (d, J=7.5 Hz, 1 H), 4.18 (dd, J=5.0, 4.5 Hz, 2 H),3.83-3.81 (br m, 2H), 2.91 (dd, J=8.0, 7.5 Hz, 2 H), 2.60 (s, 3H), 2.49(t, J=7.0 Hz, 2 H), 2.26-2.24 (br m, 1H), 2.09-2.03 (m, 2 H). 13C NMR(126 MHz, CDCl3): delta 173.5, 167.8, 167.8, 155.8, 155.5, 155.4, 152.5, 150.7,150.6, 149.7, 149.3, 148.6, 143.5, 137.9, 137.9, 131.8, 131.7, 130.7, 130.7,128.7, 127.9, 126.2, 125.5, 124.7, 124.7, 123.3, 123.3, 122.5, 122.4, 119.5,119.4, 66.1, 61.0, 34.4, 33.4, 25.3, 21.3. IR (ATR) cm-1: 3046, 2931, 2876,1726, 1608, 1582, 1553, 1478, 1421. HRMS (ESI-TOF): calcd forC39H36IrN4O3 [M-PF6]+ 801.2417, found 801.2421.

References: [1]Nucleosides, nucleotides and nucleic acids,2020,vol. 39,p. 69 - 81.

Historical Records

Technical Information

• Arndt-Eistert Homologation • Hunsdiecker-Borodin Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Ugi Reaction

Related Functional Groups of
[ 114527-28-5 ]

Carboxylic Acids

A123194 [102879-51-6]

4-(Pyridin-2-yl)butanoic acid

Similarity: 0.85

A569289 [15197-75-8]

3-(2-Pyridyl)propionic Acid

Similarity: 0.85

A566592 [848093-05-0]

2-(5-Methylpyridin-2-yl)acetic acid

Similarity: 0.83

A129981 [1201194-56-0]

2-(5-Methylpyridin-2-yl)acetic acid hydrochloride

Similarity: 0.82

A185672 [1268444-68-3]

1-(Pyridin-3-yl)cyclopropanecarboxylic acid hydrobromide

Similarity: 0.79

Related Parent Nucleus of
[ 114527-28-5 ]

Pyridines

A123194 [102879-51-6]

4-(Pyridin-2-yl)butanoic acid

Similarity: 0.85

A569289 [15197-75-8]

3-(2-Pyridyl)propionic Acid

Similarity: 0.85

A566592 [848093-05-0]

2-(5-Methylpyridin-2-yl)acetic acid

Similarity: 0.83

A129981 [1201194-56-0]

2-(5-Methylpyridin-2-yl)acetic acid hydrochloride

Similarity: 0.82

A185672 [1268444-68-3]

1-(Pyridin-3-yl)cyclopropanecarboxylic acid hydrobromide

Similarity: 0.79

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CAS No.: 114527-28-5

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