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Chemical Structure| 7379-35-3
Chemical Structure| 7379-35-3
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Product Details of [ 7379-35-3 ]

CAS No. :7379-35-3 MDL No. :MFCD00012829
Formula : C5H5Cl2N Boiling Point : -
Linear Structure Formula :- InChI Key :XGAFCCUNHIMIRV-UHFFFAOYSA-N
M.W : 150.01 Pubchem ID :81852
Synonyms :

Calculated chemistry of [ 7379-35-3 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.1
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.08
Log Po/w (WLOGP) : -1.15
Log Po/w (MLOGP) : 1.41
Log Po/w (SILICOS-IT) : 2.15
Consensus Log Po/w : 0.9

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.64
Solubility : 0.347 mg/ml ; 0.00232 mol/l
Class : Soluble
Log S (Ali) : -1.98
Solubility : 1.57 mg/ml ; 0.0105 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.58
Solubility : 0.393 mg/ml ; 0.00262 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 7379-35-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7379-35-3 ]

* 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.

  • Upstream synthesis route of [ 7379-35-3 ]
  • Downstream synthetic route of [ 7379-35-3 ]

[ 7379-35-3 ] Synthesis Path-Upstream   1~34

  • 1
  • [ 7379-35-3 ]
  • [ 15854-87-2 ]
Reference: [1] Synlett, 2003, # 12, p. 1801 - 1804
[2] Inorganic Chemistry, 2015, vol. 54, # 12, p. 6055 - 6061
  • 2
  • [ 67-56-1 ]
  • [ 7379-35-3 ]
  • [ 63071-10-3 ]
YieldReaction ConditionsOperation in experiment
1.9 g
Stage #1: for 0.5 h; Reflux
Stage #2: for 2.5 h; Reflux
Concentrated sulfuric acid (0.25 mL) was added to a solution of 4-chloropyridine hydrochloride (3.00 g) in methanol (25 mL), followed by refluxing for 0.5 hours. An aqueous solution (25 mL) of ammonium persulfate (12.2 g) was added to the reaction mixture, followed by refluxing for 2.5 hours. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. A sodium carbonate aqueous solution was added to the obtained residues, and the resultant product was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residues were purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1), whereby (4-chloro pyridin-2-yl)methanol (1.90 g) was obtained
Reference: [1] Patent: US2016/168139, 2016, A1, . Location in patent: Paragraph 0983-0985
  • 3
  • [ 7379-35-3 ]
  • [ 63071-13-6 ]
Reference: [1] Patent: US2016/168139, 2016, A1,
  • 4
  • [ 106-39-8 ]
  • [ 7379-35-3 ]
  • [ 5957-96-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 11 - 23
  • 5
  • [ 7379-35-3 ]
  • [ 62-53-3 ]
  • [ 22961-45-1 ]
YieldReaction ConditionsOperation in experiment
40% With potassium carbonate In isopropyl alcohol for 24 h; Reflux; Green chemistry General procedure: A mixture of the corresponding aryl amine (9.74 mmol), 4-chloropyridin-1-ium chloride (1.21 g,8.12 mmol), anhydrous potassium carbonate (3.45 g, 25 mmol) and supported Cu(I) catalyst (100 mg,0.22 mmol of Cu, 2.7 mol percent of Cu) was refluxed in isopropyl alcohol (40 mL) for 24 h under openatmosphere conditions. After 24 h, reaction mixture was filtered to remove potassium salts andcatalyst. The solid was stirred in 50 mL of water until dissolution of potassium salts, catalyst wasfiltered off, washed twice with water (10 mL), methanol (10 mL), dried in vacuum and stored forfurther use. Diethyl ether (100 mL) was added to the product containing filtrate and the solutionwas then washed with 100 mL of water (three times). Organic phase was dried using anhydroussodium sulfate and solvents were removed under reduced pressure. Product(s) was/were separatedby flash chromatography on silica gel using methanol-dichloromethane (1:9) mixture as a mobile phase.Yields of products are listed in Table 2.
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7729 - 7737
[2] Molecules, 2017, vol. 22, # 1,
  • 6
  • [ 7379-35-3 ]
  • [ 108-95-2 ]
  • [ 4783-86-2 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 29, p. 5045 - 5048
[2] Patent: US6500948, 2002, B1,
[3] Patent: US6153757, 2000, A,
[4] Patent: US6750228, 2004, B1,
[5] Tetrahedron Letters, 2010, vol. 51, # 2, p. 248 - 251
[6] Patent: US2010/174089, 2010, A1, . Location in patent: Page/Page column 4
  • 7
  • [ 110-89-4 ]
  • [ 7379-35-3 ]
  • [ 2767-90-0 ]
Reference: [1] European Journal of Medicinal Chemistry, 2001, vol. 36, # 3, p. 215 - 225
[2] Synlett, 2000, # 1, p. 116 - 118
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 21, p. 6122 - 6126
[4] Tetrahedron Letters, 2004, vol. 45, # 4, p. 757 - 759
[5] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 2627 - 2645
  • 8
  • [ 7379-35-3 ]
  • [ 100-51-6 ]
  • [ 49826-70-2 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 5℃; for 0.25 h;
Stage #2: at 5 - 60℃;
A flask is charged with NaH (60percent dispersion in mineral oil, 0.72 g, 18.0 mmol) then suspended in DMF (30 mL) and cooled to 5° C. To this mixture is added benzyl alcohol (1.04 mL, 10.0 mmol) drop-wise. The mixture is stirred for 15 minutes then 4-chloropyridine-HCl (1.00 g, 6.67 mmol) is added in three portions over 5 min. The resulting mixture is stirred at 5° C. for 10 min then warmed to 60° C. and stirred for 1.5 h. The mixture is then cooled to 23° C., treated with water, and extracted with EtOAc. The combined organics are dried with MgSO4, filtered, and concentrated in vacuo. Purification of the crude by flash chromatography (SiO2, 5percent EtOAc in hexanes to 50percent EtOAc in hexanes) gives the title intermediate (1.10 g, 89percent).
89%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 5℃; for 0.25 h;
Stage #2: at 5 - 60℃; for 1.75 h;
Example 3
Synthesis of 4-(benzyloxy)pyridine.
A flask is charged with NaH (60percent dispersion in mineral oil, 0.72 g, 18.0 mmol) then suspended in DMF (30 mL) and cooled to 5 °C.
To this mixture is added benzyl alcohol (1.04 mL, 10.0 mmol) drop-wise.
The mixture is stirred for 15 minutes then 4-chloropyridine-HCl (1.00 g, 6.67 mmol) is added in three portions over 5 min.
The resulting mixture is stirred at 5 °C for 10 min then warmed to 60 °C and stirred for 1.5 h.
The mixture is then cooled to 23 °C, treated with water, and extracted with EtOAc.
The combined organics are dried with MgSO4, filtered, and concentrated in vacuo.
Purification of the crude by flash chromatography (SiO2, 5percent EtOAc in hexanes to 50percent EtOAc in hexanes) gives the title intermediate (1.10 g, 89percent).
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 24, p. 13756 - 13767
[2] Patent: US2011/275627, 2011, A1, . Location in patent: Page/Page column 60
[3] Patent: EP2331541, 2011, A1, . Location in patent: Paragraph 0070; 0071
[4] Patent: EP2331541, 2015, B1, . Location in patent: Paragraph 0070; 0071
  • 9
  • [ 7379-35-3 ]
  • [ 123-30-8 ]
  • [ 102877-78-1 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydroxide In dimethyl sulfoxide at 100℃; for 18 h; A solution of 4-chloropyridine hydrochloride (Aldrich, 3.0 g, 20.0 mmol) in dimethyl sulfoxide (40 mL) was treated with 4-aminophenol (Aldrich, 2.1 g, 20.0 mmol) and sodium hydroxide pellets (2.0 g, 50.0 mmol) and the mixture was heated at 100° C. for 18 h. The mixture was cooled to room temperature, poured onto a mixture of ice-water (300 g) and extracted with Et2O (3.x.150 mL). The combined extracts were washed with brine, dried (MgSO4) and concentrated to give the 4-(4-aminophenoxy)aniline as a pale yellow solid (3.5 g, 94percent). 1H NMR (DMSO-d6) δ 8.38 (dd, 2H, J=5.5, 1.5 Hz), 6.83-6.79 (m, 4H), 6.63-6.59 (m, 2H), 5.13 (br s, 2H); MS (ESI+) m/z 187.2 (M+H)+.
67% With sodium hydroxide In dimethyl sulfoxide at 100℃; for 16 h; Step 1. 4-(Pyridin-4-yloxy) aniline. To a solution of 4-chloropyridine hydrochloride (1.0 g, 6.67 mmol), 4-aminophenol (0.73 g, 6.67 mmol) in 15 niL of DMSO was added NaOH (0.67 g, 16.67 mmol). The reaction mixture was stirred at 100°C for 16 hr and cooled to r.t. The resulting mixture was diluted with water and extracted with EtOAc. Combined organic layers were dried over anhydrous Na2S04 and concentrated. The residue was purified by column chromatography to give 4-(pyridin-4-yloxy)aniline (0.83 g, 67percent yield) as a pale yellow solid. LC-MS: m/z: 187(M+H)+.
Reference: [1] Patent: US2005/245530, 2005, A1, . Location in patent: Page/Page column 23
[2] Patent: WO2014/176258, 2014, A1, . Location in patent: Page/Page column 32
[3] Patent: WO2003/99771, 2003, A2, . Location in patent: Page 55
  • 10
  • [ 124-38-9 ]
  • [ 7379-35-3 ]
  • [ 10177-29-4 ]
YieldReaction ConditionsOperation in experiment
57%
Stage #1: With sodium carbonate In water
Stage #2: With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere
Stage #3: at 20℃; for 12 h; Inert atmosphere
4-Chloropyridine hydrochloride (25 g) is neutralized with aq. Na2C03 (10percent) and extracted with DCM. The organic layer is separated, dried over Na2S04 and concentrated under reduced pressure to afford 4-chloropyridine (19 g). To a solution of diisopropylamine (31 ml_, 217.6 mmol) in dry THF is added n-butyllithium (1 15 ml_, 184.1 mmol) dropwise at -78°C under nitrogen. After 30 min, a solution of 4-chloropyridine (19 g, 167.4 mmol) in dry THF is slowly added under nitrogen. The reaction mixture is futher stirred for 1 h at -78°C before addition of solid C02, let warmed to RT and stirred at RT for 12 h under nitrogen. After this time, reaction mixture is concentrated under reduced pressure and acidified with aq. HCI solution (1 .5 N) under ice-cooled condition. Precipitate is filtered under reduced pressure and dried overnight under vacuum to afford 15 g (57percent) of the title compound. 1H NMR (DMSO-c/6, 400 MHz): δ 13.83 (bs, 1 H), 8.92 (s, 1 H), 8.64-8.63 (d, J = 5.4 Hz, 1 H), 7.66-7.65 (d, J = 5.4 Hz, 1 H).
Reference: [1] Patent: WO2011/58149, 2011, A1, . Location in patent: Page/Page column 123-124
  • 11
  • [ 7379-35-3 ]
  • [ 10177-29-4 ]
Reference: [1] Patent: US2011/53975, 2011, A1,
  • 12
  • [ 7379-35-3 ]
  • [ 142-84-7 ]
  • [ 69008-70-4 ]
YieldReaction ConditionsOperation in experiment
81.2% at 110℃; for 8 h; Large scale Dipropylamine 90 kg was drawn into a 200 L reaction shaft,Add 4-chloropyridine hydrochloride 30kg,Potassium fluoride 12kg, the temperature was raised to 110 , incubated for 8 hours,Decompression recovery dipropylamine, sodium bicarbonate solution while hot to adjust the pH to about 8, adding petroleum ether 150kg,Separation of the water layer, the organic layer cooling, filtration, drying too28.9 kg of 4-dipropylaminopyridine,Purity 98.1percent, yield 81.2percent.
Reference: [1] Patent: CN107501173, 2017, A, . Location in patent: Paragraph 0020
[2] European Journal of Organic Chemistry, 2013, # 24, p. 5423 - 5430
  • 13
  • [ 123-75-1 ]
  • [ 7379-35-3 ]
  • [ 2456-81-7 ]
Reference: [1] Synlett, 2000, # 1, p. 116 - 118
[2] Tetrahedron Letters, 2001, vol. 42, # 33, p. 5689 - 5692
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 21, p. 6122 - 6126
[4] Tetrahedron Letters, 2004, vol. 45, # 4, p. 757 - 759
  • 14
  • [ 111-86-4 ]
  • [ 7379-35-3 ]
  • [ 64690-19-3 ]
YieldReaction ConditionsOperation in experiment
78.5% at 130℃; for 2 h; Large scale Into 200L reactor was pumped n-octylamine 100kg,30kg of 4-chloropyridine hydrochloride and 10kg of sodium fluoride were added, the temperature was raised to 130 ° C, and the mixture was stirred for 2 hours while keeping warm,Decompression recovery n-octylamine, while hot sodium carbonate aqueous solution to adjust the pH to about 7, adding ethyl acetate 120kg, separating the aqueous layer, the organic layer was cooled, filtered,Dried to give 4-octylaminopyridine 32.3kg,Purity was 99.3percent, yield was 78.5percent.
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6586 - 6596
[2] Patent: CN107501173, 2017, A, . Location in patent: Paragraph 0018
  • 15
  • [ 142-95-0 ]
  • [ 7379-35-3 ]
  • [ 64690-19-3 ]
YieldReaction ConditionsOperation in experiment
93% at 120 - 200℃; for 7 h; 5.0 g (0.0333 mol) of 4-chlororpyridine hydrochloride,And 0.55 g (0.0333 mol) of n-OCtylaminehydrochloride,The mixture is stirred and heated from 120 ° C to 180 ° C, heated to 200 ° C and held for 7 hours. The reaction was confirmed by thin-layer chromatography, and after completion, it was cooled and cooled to 100 ° C. To the reaction solution was added 20 ml of water and the mixture was cooled with stirring.To the reaction mixture was added 35percent aqueous solution of sodium hydroxide to make it alkaline. The mixture was extracted three times with 20 ml of di-dichloromethane (MC). The organic layer was collected, washed with 10 ml of cold water, washed with saturated brine, dehydrated with magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure, 14 ml of hexane was added to the residue solid, and the mixture was refluxed and cooled. The resulting crystals were filtered, dried under reduced pressure at room temperature. [0103] 6.4 g of octylaminopyridine base (yield: 93.0percent, MP 65-69 ° C) was obtained through the above-mentioned procedure.
Reference: [1] Patent: KR2017/13425, 2017, A, . Location in patent: Paragraph 0099; 0100
[2] Patent: US4206215, 1980, A,
  • 16
  • [ 110-85-0 ]
  • [ 7379-35-3 ]
  • [ 1008-91-9 ]
Reference: [1] Molecules, 2017, vol. 22, # 1,
  • 17
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  • [ 89167-34-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2008, vol. 47, # 5, p. 888 - 890
[2] Organic and biomolecular chemistry, 2003, vol. 1, # 23, p. 4254 - 4261
  • 18
  • [ 7379-35-3 ]
  • [ 189449-41-0 ]
Reference: [1] Synlett, 2013, vol. 24, # 1, p. 49 - 52
  • 19
  • [ 504-24-5 ]
  • [ 1412913-76-8 ]
  • [ 7379-35-3 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2012, vol. 48, # 8, p. 1235 - 1250[2] Khim. Geterotsikl. Soedin., 2012, vol. 48, # 8, p. 1235 - 1250,16
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  • [ 52725-10-7 ]
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Reference: [1] Chemische Berichte, 1899, vol. 32, p. 1309
  • 21
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  • [ 20815-52-5 ]
Reference: [1] Patent: US4939159, 1990, A,
  • 22
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  • [ 20815-52-5 ]
Reference: [1] European Journal of Pharmaceutical Sciences, 2013, vol. 49, # 4, p. 603 - 613
  • 23
  • [ 7379-35-3 ]
  • [ 68-12-2 ]
  • [ 114077-82-6 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran
Stage #2: at 20℃;
Example 18; Preparation of ter?-butyl-2-((4-mercaptopyridin-3-yl)methylthio)ethyl carbamate; ), DMF ) c H3OH h; Step 1 : LDA (0.11 mmol) was added to 4-chloropyridine 1 (15 g, 0.1 mol) in THF (250 mL) dropwise at -6O0C and stirred at this temperature for 1 hr. Then, DMF (9.3 mL, 0.12 mol) was added and stirred at rt overnight. The product was extracted with ethyl acetate from water. The combined organic layer was dried(Na2SO4), filtered and concentrated. The residue was purified by column chromatography (PE:EA = 10:1) to afford 4.6 g white solid, yield 65percent. 1H NMR (400 MHz, CDCl3):10.51 (s, IH), 9.05 (s, IH), 8.08 (d, IH), 7.45 (d, IH).
65%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at 20℃;
Step 1: LDA (0.11 mmol) was added to 4-chloropyridine 1 (15 g, 0.1 mol) in THF (250 mL) dropwise at -60°C and stirred at this temperature for 1 h. Then, DMF (9.3 mL, 0.12 mol) was added and stirred at room temperature overnight. The product was extracted with EA from water. The combined organic layer was dried(Na2SCU), filtered and concentrated. The residue was purified by column <n="90"/>chromatography (P.E/EA 10:1) to afford 4.6 g white solid, yield 65percent. 1HNMR (400MHz, CDCl3): 10.51 (s, 1H), 9.05 (s, 1H), 8.08 (d, 1H), 7.45 (d, 1H).
36%
Stage #1: With sodium hydrogencarbonate In diethyl ether for 1 h;
Stage #2: With lithium diisopropyl amide In tetrahydrofuran at -78 - -40℃; for 1 h;
Stage #3: at -78 - 20℃; for 18 h;
Saturated NaHCO3 was added to a suspension of 4-chloropyridinium hydrochloride (10 g, 67 mmol) in diethyl ether (100 mL).The biphasic mixture was stirred for 1 h, then separated. The aqueous layer was extracted with diethyl ether (3 x 50 mL). Combined organic layers were dried over Na2SO4 andconcentrated. The resulting oil was purified by distillation to afford pure 4-chloropyridine.A -78 °C solution of 2 M lithium diisopropylamide (LDA) in heptane/tetrahydrofuran (THF)(19 mL, 38.04 mmol, 1.2 equiv.) was diluted in THF (60 mL) and treated with the dropwiseaddition of a solution of 4-chloropyridine (3.6 g, 31.7 mmol, 1 equiv.) in THF (10 mL). Themixture was slowly warmed to -40 °C and stirred 1 h before returning to -78 °C. Dimethylformamide (DMF, 3.0 mL, 38.04 mmol, 1.2 equiv.) was added, and the reaction was stirred 2 h at -78 °C, then warmed to RT as ice bath expired and stirred 16 h. The reaction was cooled to -10 °C and quenched with sat. NH4C1 (5 mL). The reaction wasdiluted with water and extracted with ethyl acetate. The organic layers were washed with brine, dried over Na2SO4 and concentrated. The crude red oil was purified by silica gel chromatography (30percent EtOAc/hexanes) to afford the title compound as a yellow tinted oil which crystalized to clear needles under argon (1.6 g, 36percent yield). Spectra matched the literature reports. ‘H-NIVIR (400 IVIHz, CDC13): = 10.51 (s, 1 H); 9.05 (s, 1 H); 8.68 (d, J5.76 Hz, 1 H); 7.43 (d, J 5.4 Hz, 1 H).
Reference: [1] Patent: WO2010/30811, 2010, A2, . Location in patent: Page/Page column 73-74
[2] Patent: WO2009/55696, 2009, A1, . Location in patent: Page/Page column 87-88
[3] Heterocycles, 2006, vol. 67, # 2, p. 543 - 547
[4] Patent: WO2018/152329, 2018, A1, . Location in patent: Page/Page column 50; 51
[5] Patent: US2010/75981, 2010, A1, . Location in patent: Page/Page column 7-8
[6] Synlett, 2013, vol. 24, # 1, p. 49 - 52
  • 24
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  • [ 7379-35-3 ]
  • [ 109-94-4 ]
  • [ 114077-82-6 ]
YieldReaction ConditionsOperation in experiment
21% With diisopropylamine In tetrahydrofuran; sodium hydrogencarbonate EXAMPLE 21
N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]thieno[3,2-c]pyridine-2-carboxamide Dihydrochloride
Preparation of the Acid:
4-Chloropyridine hydrochloride (15 g, 99.9 mmol) is free-based by stirring in 1000 mL 1:1 saturated NaHCO3/ether for 1 h.
The layers are allowed to separate, the aqueous layer is extracted with ether (2*175 mL), and the combined organic layer is dried over MgSO4, filtered, and concentrated to an oil. THF (300 mL) is chilled to -70° C. in a dry flask. N-butyllithium (105.1 mL, 168.2 mmol) is added drop-wise, and the mixture is placed in an ice bath.
Diisopropylamine (23.6 mL. 168.4 mmol) in THF (50 mL) is added drop-wise, the yellow solution is stirred for 30 min, and the reaction is cooled to -70° C. The free-based 4-chloropyridine oil (9.55 g, 84.1 mmol) is dissolved in THF (50 mL) and added drop-wise to the chilled yellow solution, that turned dark red after the addition.
The reaction is stirred at -70° C. for 2 h.
Ethyl formate (13.6 mL, 168.3 mmol) in THF (25 mL) is then added drop-wise to the dark solution at -70° C.
After 2 hours, the reaction is warmed to -10° C. and quenched with water (450 mL).
The layers are allowed to separate, and the aqueous layer is extracted with ether (3*200 mL).
The combined organic layer is dried over MgSO4, filtered, and concentrated in vacuo to an oil.
The crude material is chromatographed over 320 g slurry-packed silica eluding with 30percent EtOAc/hexane.
The fractions with the desired compound are collected and concentrated to an orange oil which solidified under vacuum, affording 4-chloropyridine-3-carboxaldehyde (C140) as an orange solid (21percent yield).
Reference: [1] Patent: US2003/45540, 2003, A1,
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  • [ 114077-82-6 ]
Reference: [1] Patent: US2002/193596, 2002, A1,
  • 26
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  • [ 114077-82-6 ]
Reference: [1] Patent: US2011/53975, 2011, A1,
  • 27
  • [ 1126-09-6 ]
  • [ 7379-35-3 ]
  • [ 121912-29-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 21, p. 4838 - 4841
[2] Patent: US2001/56123, 2001, A1,
[3] Patent: US2002/193348, 2002, A1,
[4] Patent: EP976722, 2000, A1,
[5] Patent: EP1065200, 2001, A1,
[6] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8696 - 8711
  • 28
  • [ 7379-35-3 ]
  • [ 121912-29-6 ]
Reference: [1] Tetrahedron, 1988, vol. 44, # 23, p. 7095 - 7108
  • 29
  • [ 1126-09-6 ]
  • [ 64-17-5 ]
  • [ 7379-35-3 ]
  • [ 121912-29-6 ]
Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 40, p. 4521 - 4524
  • 30
  • [ 7379-35-3 ]
  • [ 126832-81-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 10, p. 3586 - 3604
  • 31
  • [ 5382-16-1 ]
  • [ 7379-35-3 ]
  • [ 130658-65-0 ]
Reference: [1] Patent: US4968704, 1990, A,
  • 32
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  • [ 927-74-2 ]
  • [ 192643-83-7 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 10, p. 1717 - 1720
  • 33
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  • [ 224178-65-8 ]
Reference: [1] Patent: WO2012/126984, 2012, A1,
  • 34
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  • [ 191602-60-5 ]
Reference: [1] Organic Process Research and Development, 2003, vol. 7, # 3, p. 436 - 445
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Chemical Structure| 877399-50-3

[ 877399-50-3 ]

tert-Butyl 4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylate

Chemical Structure| 73183-34-3

[ 73183-34-3 ]

4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi(1,3,2-dioxaborolane)

Chemical Structure| 15128-82-2

[ 15128-82-2 ]

2-Nitropyridin-3-ol

Related Functional Groups of
[ 7379-35-3 ]

Chlorides

Chemical Structure| 19524-08-4

[ 19524-08-4 ]

4-Chloro-3-methylpyridine hydrochloride

Similarity: 0.87

Chemical Structure| 55934-00-4

[ 55934-00-4 ]

3,4-Dichloropyridine

Similarity: 0.85

Chemical Structure| 3678-63-5

[ 3678-63-5 ]

4-Chloro-2-picoline

Similarity: 0.83

Chemical Structure| 626-60-8

[ 626-60-8 ]

3-Chloropyridine

Similarity: 0.81

Chemical Structure| 26452-80-2

[ 26452-80-2 ]

2,4-Dichloropyridine

Similarity: 0.80

Related Parent Nucleus of
[ 7379-35-3 ]

Pyridines

Chemical Structure| 19524-08-4

[ 19524-08-4 ]

4-Chloro-3-methylpyridine hydrochloride

Similarity: 0.87

Chemical Structure| 55934-00-4

[ 55934-00-4 ]

3,4-Dichloropyridine

Similarity: 0.85

Chemical Structure| 3678-63-5

[ 3678-63-5 ]

4-Chloro-2-picoline

Similarity: 0.83

Chemical Structure| 626-60-8

[ 626-60-8 ]

3-Chloropyridine

Similarity: 0.81

Chemical Structure| 26452-80-2

[ 26452-80-2 ]

2,4-Dichloropyridine

Similarity: 0.80