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Structure of 475275-69-5

Chemical Structure| 475275-69-5

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Product Details of [ 475275-69-5 ]

CAS No. :475275-69-5
Formula : C6H7BClNO3
M.W : 187.39
SMILES Code : COC1=NC=C(Cl)C(B(O)O)=C1
MDL No. :MFCD06658398
InChI Key :ONFAPGPPGOLJST-UHFFFAOYSA-N
Pubchem ID :11030558

Safety of [ 475275-69-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 475275-69-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.17
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 45.56
TPSA ?

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

62.58 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

0.69
Log Po/w (WLOGP)?

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

-0.58
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.

-0.57
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

-0.55
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.2

Water Solubility

Log S (ESOL):?

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

-1.67
Solubility 3.96 mg/ml ; 0.0212 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.

-1.58
Solubility 4.91 mg/ml ; 0.0262 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

-1.66
Solubility 4.09 mg/ml ; 0.0218 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.

-6.95 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

1.0
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)

2.12

Application In Synthesis of [ 475275-69-5 ]

* 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 [ 475275-69-5 ]

[ 475275-69-5 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 109-04-6 ]
  • [ 475275-69-5 ]
  • 5'-chloro-2'-methoxy-[2,4']bipyridinyl [ No CAS ]
  • 2
  • [ 13473-01-3 ]
  • [ 475275-69-5 ]
YieldReaction ConditionsOperation in experiment
General procedure: [0548] At -78 C., LDA (2 molar in THFheptane/ethylbenzene)was added to a solution of the appropriate pyridinederivative in THF (3 ml/mmol), the mixture was stirred for2-4 h and triisopropyl borate was then added quickly. Thereaction mixture was maintained at -7S C. for a further 2-3hand then slowly thawed to RT overnight. After addition ofwater, the THF was removed under reduced pressure and theaqueous phase was extracted twice with ethyl acetate Theaqueous phase was acidified with 2M hydrochloric acid, generallyresulting in formation of a precipitate which was filteredoff, washed with water and dried. The aqueous phasewas extracted three times with ethyl acetate. The combinedorganic phases were dried (sodium sulphate), filtered andconcentrated under reduced pressure.
  • 3
  • [ 13195-50-1 ]
  • [ 475275-69-5 ]
  • 5-chloro-2-methoxy-4-(5-nitrothien-2-yl)-pyridine [ No CAS ]
  • 4
  • [ 4522-35-4 ]
  • [ 475275-69-5 ]
  • [ 1621525-22-1 ]
YieldReaction ConditionsOperation in experiment
With dmap; copper diacetate; caesium carbonate; In 1,4-dioxane; at 80℃; INTERMEDIATE 29 5-Chloro-4-(3-iodo-lH-pyrazol-l-yl)-2-methoxypyridine A solution of 3-iodo-lH-pyrazole (0.3 g, 1.547 mmol), 5-chloro-2-methoxypyridine- 4-boronic acid (0.377 g, 2.011 mmol), DMAP (0.756 g, 6.19 mmol), copper(II)acetate (0.281 g, 1.547 mmol), and cesium carbonate (1.26 g, 3.87 mmol) in 1,4-dioxane (7.73 mL) was heated at 80 C overnight. The reaction was allowed to warm to room temperature and filtered. The filtrate was diluted with EtOAc and water, and the seperated aq. layer was extracted with EtOAc. The combined organics were dried over MgS04, filtered and concentrated. The residue was purified with flash chromatography (ISCO Combiflash, 24 g, 0-10 % EtOAc in hexanes) to give 5- chloro-4-(3-iodo-lH-pyrazol-l-yl)-2-methoxypyridine, as a white solid. LCMS calc. = 335.93; found = 335.82 (M+H)+. 1H NMR (500 MHz, CDC13): delta 8.25 (s, 1 H); 8.01 (d, J= 2.6 Hz, 1 H); 7.14 (s, 1 H); 6.66 (d, J= 2.5 Hz, 1 H); 3.96 (s, 3 H).
  • 5
  • [ 1099597-32-6 ]
  • [ 475275-69-5 ]
  • 5-chloro-4-[5-chloro-2-(trifluoromethyl)phenyl]-2-methoxypyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium dihydrogenphosphate; chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); In tetrahydrofuran; water; at 60℃;Inert atmosphere; Sonication; General procedure: [0550] In a flask which had been dried by heating andflushed with argon, 1.0 eq. of the appropriate boronic acids,1.0 eq. of the aryl bromide or aryl iodide and 0.05 eq. ofXPhos precatalyst [(2'-aminobiphenyl-2-yl)( chloro )palladium/dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphane(1:1)], J. Am. Chern. Soc. 2010, 132, 14073-14075]were initially charged. The flask was then evacuated threetimes and in each case vented with argon. THF (about 12ml/mmol) which had been degassed in an ultrasonic bath and3.0 eq. of aqueous potassium phosphate solution (0.5 molar)were added, and the reaction mixture was stirred at 60 C.Water and ethyl acetate were then added to the reaction mixture.After phase separation, the aqueous phase was extractedonce with ethyl acetate. The combined organic phases weredried (sodium sulphate), filtered and concentrated underreduced pressure. The crude product was then purified eitherby flash chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate mixtures or dichloromethane/methanolmixtures) or by preparative HPLC (Reprosil CIS, water/acetonitrilegradient or water/methanol gradient).
193 mg With potassium phosphate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In tetrahydrofuran; water; at 60℃;Inert atmosphere; Sonication; General procedure: General Method 2B: Suzuki coupling In a flask whichhad been dried by heating and flushed with argon, 1.0 eq. of the appropriateboronic acids, 1.0 eq. of the aryl bromide or aryl iodide and 0.05 eq. of XPhosprecatalyst[(2'-aminobipheny1-2-y1)(chloro)palladium/dicyclohexyl(2',4',61-triisopropylbipheny1-2-yl)phosphane(1:1)], J. Am. Chem. Soc. 2010, 132, 14073-14075] were initially charged. Theflask was then evacuated three times and in each case vented with argon. THF(about 12 ml/mmol) which had been degassed in an ultrasonic bath and 3.0 eq. ofaqueous potassium phosphate solution (0.5 molar) were added, and the reactionmixture was stirred at 60 C. Water and ethyl acetate were then I uiu fore=countries added to the reaction mixture. After phase separation, the aqueousphase was extracted once with ethyl acetate. The combined organic phases weredried (sodium sulphate), filtered and concentrated = under reduced pressure.The crude product was then purified either by flash chromatography (silica gel60, mobile phase: cyclohexane/ethyl acetate mixtures ordichloromethane/methanol mixtures) or by preparative HPLC (Reprosil C18,water/acetonitrile gradient or water/methanol gradient).443 mg (2.20 mmol) of5-chloro-2-methoxypyridin-4-ylboronic acid and 571 mg (2.20 mmol) of2-bromo-4-chloro-1-(trifluoromethyl)benzene in the presence of XPhosprecatalyst were reacted according to General Method 2B.Yield: 193 mg (purity 93%, 25% of theory)
  • 6
  • [ 13473-01-3 ]
  • [ 5419-55-6 ]
  • [ 475275-69-5 ]
YieldReaction ConditionsOperation in experiment
10.44 g With lithium hexamethyldisilazane; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 - 20℃; General procedure: General Method 1A: Preparation of a boronic acid At-78C, LDA (2 molar in THF/heptane/ethylbenzene) was added to a solution of theappropriate pyridine derivative in THF (3 ml/mmol), the mixture was stirred for2-4 h and triisopropyl borate was then added quickly. The reaction mixture wasmaintained at -78 C for a further 2-3 h and then slowly thawed to RT overnight.After addition of water, the THF was removed under reduced pressure and theaqueous phase was extracted twice with ethyl acetate The aqueous phase wasacidified with 2M hydrochloric acid, generally resulting in formation of aprecipitate which was filtered off, washed with water and dried. The aqueousphase was extracted three times with ethyl acetate. The combined organic phaseswere dried (sodium sulphate), filtered and concentrated under reduced pressure.10.0 g (69.65 mmol) of 5-chloro-2-methoxypyridine werereacted according to General Method 1A.The desired product precipitated on acidification with hydrochloric acid (2N).Yield: 10.44 g (purity 91%, 73% of theory)
10.0 g of 5-chloro-2-methoxypyridine were initially charged in 225 ml of THF, and 41.8 ml (83.6 mmol) of lithium diisopropylamide (2M in THF/heptane/ethylbenzene) were added at -78 C. The mixture was stirred at -78 C. for 4 h, and 32.6 ml (141 mmol) of triisopropyl borate were then added rapidly. The reaction mixture was stirred at-78 C. for 3 h and then warmed to room temperature overnight. The procedure was then repeated, and a further 20.9 ml (41.8 mmol) of lithium diisopropylamide (2M in THF/heptane/ethylbenzene) and 16.1 ml (69.7 mmol) of triisopropyl borate were added. The reaction mixture was poured into 500 ml of water and THF was removed under reduced pressure. The aqueous phase was extracted three times with ethyl acetate. The aqueous phase was acidified with hydrochloric acid (2N) and the precipitate was filtered oil. The filtrate was extracted twice with ethyl acetate, the organic phase was dried and filtered, the solvent was removed under reduced pressure and the residue, together with the precipitate, was dried under high vacuum. Yield:10.4 g (91% pure, 73% of theory).j0675] LC/MS [Method 1]: R=0.50 mm; MS (ESIpos):mlz=188 (M+H), j0676] ?H-NMR (400 MHz, DMSO-d5): oe [ppm]=8.64(br. s, 2H), 8.12 (s, 1H), 6.81 (s, 1H), 3.82 (s, 3H).
16 g Under a nitrogen atmosphere, 300 g of anhydrous tetrahydrofuran was added to the reaction flask, stirring was continued, 17 g of 5-chloro-2-methoxypyridine was added and cooled to -30C.A solution of 70 mL of 2.0 M of n-BuLi was slowly added dropwise, and after stirring for 30 minutes, 1,3 g of 1,4,7,10-tetramethyl-1,4,7,10-tetraazacyclododecane was slowly added dropwise.After 2 hours of incubation, 41 mL of triisopropyl borate was slowly added dropwise at -30 C, stirred for 1 hr, slowly raised to room temperature and stirred for 1 hour.And 400 g of concentrated hydrochloric acid was added thereto, followed by stirring for 1 hour to carry out a hydrolysis reaction.The layers were allowed to stand, and the organic layer was washed three times with water (3 x 100 g).The aqueous layers were combined and the aqueous layer was extracted once with 100 ml of petroleum ether. The combined organic layers were dried over 50 g of anhydrous sodium sulfate and filtered.The filtrate was concentrated to dryness to give 6-chloro-2-methoxy-4-pyridine boronic acid 16 g,
  • 7
  • [ 1214348-81-8 ]
  • [ 475275-69-5 ]
  • 5-chloro-4-[5-chloro-2-(difluoromethoxy)phenyl]-2-methoxypyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With catacxium A; In tetrahydrofuran; water; at 60℃; for 1h; At 60 C., 4.17 g (16.2 mmol) of 2-bromo-4- chioro-1 -(difluoromethoxy)benzene, 3.04 g (16.2 mmol) of <strong>[475275-69-5](5-chloro-2-methoxypyridin-4-yl)boronic acid</strong>, 561 mg (486 tmol) of CATAXCium A precatalyst and 133 ml of aqueous potassium phosphate solution (0.5N) were stirred in 73 ml of THF for 1 h. The reaction mixture was then diluted with 125 ml of water and 125 ml of ethyl acetate. The phases were separated and the aqueous phase was extracted with 125 mlof ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. Purification by colunm chromatography of the crude product (100 g silica cartridge, flow rate:50 ml/min, cyclohexane/ethyl acetate gradient) gave the title compound. Yield: 2.80 g (86% pure, 46% of theory).10679] LC/MS [Method 1]: R=1.20 mm; MS (ESIpos):mlz=320 (M+H).
  • 8
  • [ 1214348-81-8 ]
  • [ 475275-69-5 ]
  • 5-chloro-4-[5-chloro-2-(difluoromethoxy)phenyl]pyridin-2(1H)-one [ No CAS ]
  • 9
  • [ 13473-01-3 ]
  • [ 121-43-7 ]
  • [ 475275-69-5 ]
YieldReaction ConditionsOperation in experiment
16 g Under a nitrogen atmosphere, 300 g of anhydrous tetrahydrofuran was added to the reaction flask, stirring was continued, 17 g of 5-chloro-2-methoxypyridine was added and cooled to -30C.Sulfur was added dropwise to 70 mL of 2.0 M of n-BuLi. After stirring for 30 minutes, 26 g of 1,4,7-trimethyl-1,4,7-triazacyclononane was slowly added dropwise.After incubation for 2 hours, 26 mL of trimethyl borate was slowly added dropwise at -30 C, stirred for 1 hr, slowly rose to room temperature and stirred for 1 hour.And 400 g of concentrated hydrochloric acid was added thereto, followed by stirring for 1 hour to carry out a hydrolysis reaction.The layers were allowed to stand, and the organic layer was washed three times with water (3 x 100 g).The aqueous layers were combined and the aqueous layer was extracted once with 100 ml of petroleum ether. The combined organic layers were dried over 50 g of anhydrous sodium sulfate and filtered.The filtrate was concentrated to dryness to give 16 g of product 5-chloro-2-methoxy-4-pyridine boronic acid.
YieldReaction ConditionsOperation in experiment
General procedure: To a solution of the appropriate pyridine derivative in tetrahydrofuran (about 3 ml/mmol) at -78 C. was added lithium diisopropylamide (2 M in tetrahydrofuran/heptane/ethylbenzene), the mixture was stirred for 2 to 4 h and then triisopropyl borate was then added quickly. The reaction mixture was maintained at -78 C. for a further 2 to 3 h and then slowly thawed to RT overnight. After addition of water, the tetrahydrofuran was removed under reduced pressure and the aqueous phase was extracted twice with ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2M), generally resulting in formation of a precipitate which was filtered off, washed with water and dried. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure.
General procedure: [0471] To a solution of the appropriate pyridine derivativein tetrahydroffiran (about 3 ml/mmol) at -78 C. was added lithium diisopropylamide (2 M in tetrahydrofuranlheptane/ ethylbenzene), the mixture was stirred for 2 to 4 h and then triisopropyl borate was then added quickly. The reaction mixture was maintained at -78 C. for a further 2 to 3 h and then slowly thawed to RT overnight. Afier addition of water, the tetrahydroffiran was removed under reduced pressure and the aqueous phase was extracted twice with ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2M), generally resulting in formation of a precipitate which was filtered off, washed with water and dried. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure.; According to General Method 1A, 11.53 g (82.9 mmol) of 2,5-dimethoxypyridine were reacted. The desired product precipitated out after acidification of the aqueous phase.
General procedure: To a solution of the appropriate pyridine derivative in tetrahydrofuran (about 3 ml/mmol) at -78 C. was added lithium diisopropylamide (2 M in tetrahydrofuran/heptane/ethylbenzene), the mixture was stirred for 2 to 4 h and then triisopropyl borate was then added quickly. The reaction mixture was maintained at -78 C. for a further 2 to 3 h and then slowly thawed to RT overnight. After addition of water, the tetrahydrofuran was removed under reduced pressure and the aqueous phase was extracted twice with ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2M), generally resulting in formation of a precipitate which was filtered off, washed with water and dried. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure.
  • 11
  • methyl 5-bromo-3-methylpyrazine-2-carboxylate [ No CAS ]
  • [ 475275-69-5 ]
  • methyl 5-(5-chloro-2-methoxypyridin-4-yl)-3-methylpyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In tetrahydrofuran; water; at 100℃; for 2h;Inert atmosphere; To a nitrogen-purged solution of methyl 5-bromo-3-methylpyrazine-2-carboxylate (Intermediate 1, 18 g, 78 mmol), <strong>[475275-69-5](5-chloro-2-methoxypyridin-4-yl)boronic acid</strong> (17.52 g, 93 mmol) and PdCl2(dppf) (5.70 g, 7.79 mmol) in THF (200 ml) and water (40.0 ml) was added K3PO4 (49.6 g, 234 mmol) under a nitrogen atmosphere. The reaction mixture was heated to a vigorous reflux at 100 C for 2 h. Then the reaction was allowed to slowly cool to room temperature overnight with stirring. The reaction was stirred at room temperature for 72h, then partitioned between ethyl acetate (150 ml) and water (150 ml) and stirred for 30 min. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous Na2S04, filtered and evaporated to afford a crude residue. The residue was purified via column chromatography on silica gel (ISCO RediSep Gold 220g silica gel column, gradient elution with 0% to 100% EtOAc in hexanes) to give the title compound.
 

Historical Records

Technical Information

Categories

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[ 475275-69-5 ]

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Chlorides

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Related Parent Nucleus of
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Pyridines

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