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Product Details of [ 1122-62-9 ]

CAS No. :1122-62-9 MDL No. :MFCD00006303
Formula : C7H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :AJKVQEKCUACUMD-UHFFFAOYSA-N
M.W : 121.14 Pubchem ID :14286
Synonyms :

Calculated chemistry of [ 1122-62-9 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.43
TPSA : 29.96 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 0.85
Log Po/w (WLOGP) : 1.28
Log Po/w (MLOGP) : 0.13
Log Po/w (SILICOS-IT) : 1.67
Consensus Log Po/w : 1.1

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.55
Solubility : 3.38 mg/ml ; 0.0279 mol/l
Class : Very soluble
Log S (Ali) : -1.06
Solubility : 10.5 mg/ml ; 0.0866 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.31
Solubility : 0.589 mg/ml ; 0.00486 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.03

Safety of [ 1122-62-9 ]

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

Application In Synthesis of [ 1122-62-9 ]

* 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 [ 1122-62-9 ]
  • Downstream synthetic route of [ 1122-62-9 ]

[ 1122-62-9 ] Synthesis Path-Upstream   1~48

  • 1
  • [ 1122-62-9 ]
  • [ 68500-37-8 ]
  • [ 6238-12-6 ]
Reference: [1] Organic Letters, 2018,
  • 2
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Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 7, p. 3127 - 3133
  • 3
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[2] Dalton Transactions, 2018, vol. 47, # 29, p. 9701 - 9708
  • 4
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  • [ 37988-38-8 ]
Reference: [1] Organometallics, 2017, vol. 36, # 18, p. 3578 - 3588
  • 5
  • [ 1122-62-9 ]
  • [ 37988-38-8 ]
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  • 6
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  • 7
  • [ 1122-62-9 ]
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  • [ 37988-38-8 ]
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  • 9
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  • 10
  • [ 1122-62-9 ]
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Reference: [1] Organic Letters, 2018,
  • 11
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  • [ 34784-05-9 ]
  • [ 42398-73-2 ]
Reference: [1] Organic Letters, 2018,
  • 12
  • [ 1122-62-9 ]
  • [ 6831-82-9 ]
  • [ 103-74-2 ]
Reference: [1] Patent: US2002/193347, 2002, A1,
  • 13
  • [ 1122-62-9 ]
  • [ 4964-71-0 ]
  • [ 7661-55-4 ]
Reference: [1] Organic Letters, 2018,
  • 14
  • [ 1122-62-9 ]
  • [ 17356-08-0 ]
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  • 15
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  • 16
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Reference: [1] Patent: US4853027, 1989, A,
  • 18
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  • [ 4637-24-5 ]
  • [ 66521-54-8 ]
YieldReaction ConditionsOperation in experiment
51% at 90℃; for 12 h; A solution of 4.0 g (33.0 mmol, 1.0 eq.) of 1-(pyridin-2-yl)ethan-1-one in 13.1 mL (99.1 mmol, 3.0 eq,) of DMF dimethylacetal was stirred at 90 °C for 12 h. The mixture wasallowed to cool to room temperature, and the resulting precipitate was collected by filtration. The solids were washed with 2 x 5 mL of ethyl acetate and dried under high vacuum to provide, 3.0 g (17.0 mmol, 51percent) of (E)-3 -(dimethylamino)- 1 -(pyridin-2-yl)prop-2-en- 1-one.
13 g for 24 h; Reflux 12.1 g of 2-acetylpyridine was dissolved in 150 ml of toluene, 30 ml of DMF-DMA was added while stirring, and the mixture was heated to reflux for 24 hours, cooled to room temperature, concentrated to dryness under reduced pressure, and 150 ml of petroleum ether was added to the residue for stirring. Disperse, filter, filter cake washed with petroleum ether to give intermediate 13g, yellow crystals.
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  • 19
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  • [ 4637-24-5 ]
  • [ 98-86-2 ]
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  • 20
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  • [ 54123-21-6 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 14, p. 7212 - 7218
  • 21
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  • [ 56100-19-7 ]
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  • 22
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  • [ 123-73-9 ]
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  • 23
  • [ 1122-62-9 ]
  • [ 1970-80-5 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 1, p. 559 - 561
[2] RSC Advances, 2016, vol. 6, # 41, p. 35008 - 35013
  • 24
  • [ 1122-62-9 ]
  • [ 1945-84-2 ]
Reference: [1] Synlett, 2009, # 4, p. 558 - 561
  • 25
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  • [ 19959-77-4 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 52, p. 12377 - 12385
  • 26
  • [ 1122-62-9 ]
  • [ 17570-98-8 ]
YieldReaction ConditionsOperation in experiment
97.8% at 15 - 75℃; for 2 h; At 15 , the bromine (1.52mL, 9.72mmol) was slowly added dropwise to 2-acetyl-pyridine (3g, 2.78mmol) in 30percent HBr / HOAc (12mL), and after completion of the dropwise addition, the reaction solution at 40 under stirring 1h, then stirred at 75 1h. The reaction solution was cooled to 20 , to which was added Et2O (30mL), and stirred at this temperature for 30min, the resulting yellow precipitate was filtered, and the precipitate was washed with 10mL diethyl ether, and dried to (6.81g, 97.8percent).
95% at 20℃; for 23 h; Preparation 4; 2-bromo-1 -(pyridin-2-vOethanone hvdrobromide; 30percent HBr in acetic acid (100 mL) was added at RT to a stirred solution of 2- acetylpyridine (40 g, 0.33 mol) in acetic acid (100 mL). Pyridinium tribromide (116 g) was added and the resulting mixture was stirred 23 h at RT and filtered. The solid was washed with acetic acid (3 x 100 mL) and dried at 78 0C in vacuo until sublimation began, then at RT in vacuo, giving 88.0 g (95percent) of the title substance. 1H NMR (CD3OD, 400 mHz) δ 8.82 (ddd,1H, J = 0.8, 1.7, 4.6 Hz), 8.73 (id. 1H, J = 1.5, 8.0 Hz), 8.28 (ddd, 1 H, J = 1, 1, 8 Hz)1 8.14 (ddd, 1H, J = 1, 5, 8 Hz), 3.91 (A of AB, 1H, J = 11.6 Hz), 3.81 (B of AB, 1H, J = 11.6 Hz).
93% at 0 - 70℃; for 3 h; To a solution of 1-(pyridin-2-yl)ethan-1-one (3.0 g, 24.8 mmol) in HBr in AcOH (30 mL) at 0°C, bromine (3.9 g, 24.8mmol) was added drop wise and allowed the mixture to stir at 70°C for 3 hours. After TLCshowed completion, diluted the mixture with diethyl ether (50 mL) and filtered and washedwith diethyl ether to obtain 2-bromo-1-(pyridin-2-yl)ethan-1-one hydrobromide 3 (6.5 g, 93percentyield), as cream colored solid; 1H NMR (400 MHz, DMSO-d6): δ 5.02 (s, 2H), 7.73 (m, 1H),8.01 (m, 2H), 8.75 (d, J = 4.4 Hz, 1H). All data are consistent with literature values [17].
93% With bromine In tetrachloromethane for 1 h; Reflux (2-Bromoacetyl)pyridin-1-ium bromide (A): To a stuffed solution of 1-(pyridin-2- yl)ethan-1-one (2.0 g, 16.6 mmol) in Cd4 (60 ml), bromine (2.7 g, 16.60 mmol) was added dropwise. After complete addition the final reaction mixture was refluxed for 1 h. The precipitate was collected by filtration and washed 2-3 times with diethylether and dried to obtain compound A as a beige solid (2.94 g, 93percent).
87% With hydrogen bromide; pyridinium hydrobromide perbromide In acetic acid at 40℃; EXAMPLES The following Examples are intended to illustrate the scope of the present invention and should not be considered to limit it in any way. (A) Preparation of the intermediates of the formula (III EXAMPLE NO. 1 A) Synthesis of 2-bromoacetyl-pyridine hvdrobromide 100 g of 2-acetylpyridine were dissolved in 366 ml of 33percent hydrobromic acid in acetic acid; the solution was heated to 40°C and a solution of 264 g of pyridinium tribromide in 500 ml of acetic acid was added. The mixture was kept at 40°C overnight. The reaction mixture was cooled and the precipitate filtered out and washed with 200 ml of acetic acid. The precipitate was resuspended in 400 ml of THF, then filtered out and dried, giving rise to 200 g of 2-bromoacetyl-pyridine hydrobromide (yield 87percent).

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[17] Patent: WO2009/114552, 2009, A1, . Location in patent: Page/Page column 112
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  • [ 562-10-7 ]
Reference: [1] Patent: CN103524403, 2016, B,
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  • [ 616-38-6 ]
  • [ 75418-74-5 ]
YieldReaction ConditionsOperation in experiment
51%
Stage #1: With sodium hydride In cyclohexane for 0.166667 h; Heating / reflux
Stage #2: at 20℃; Heating / reflux
Stage #3: With water; acetic acid In cyclohexane at 0℃;
Step 2: Preparation of Methyl 3-oxo-3-pyridin-2-ylpropanoate; NaH (60percent suspension on mineral oil; 30g, 750 mmol, 2.5 equiv.) was suspended in cyclohexane (900 mL) and the temperature raised to reflux. To this mixture was added 2-acetyl pyridine (36 g, 300 mmol) dropwise, followed, after 10 min, by dimethyl carbonate (100 mL, 1.2 mol, 4 equiv.). The reaction mixture was heated at reflux for 4 h, stood at room temperature overnight and then cooled to 0° C. The near solid mixture was quenched by addition of AcOH (75 mL) in H2O (250 mL), then diluted with Et2O (250 mL) and stirred until all solids had dissolved. The aqueous layer was separated and extracted with Et2O (2.x.), the combined organic extracts dried (MgSO4) and concentrated under reduced pressure. The crude orange oil was distilled to give recovered 2-acetyl pyridine (40° C./0.3 mbar; 6.5 g, 18percent) and product (105° C./0.6 mbar; 27.5 g, 51percent).
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  • [ 4637-24-5 ]
  • [ 75415-03-1 ]
YieldReaction ConditionsOperation in experiment
30%
Stage #1: at 100℃; for 16 h; Reflux
Stage #2: With hydrazine hydrate In ethanol at 60℃; for 0.5 h;
A mixture of N-dimethoxymethyl-N,N-dimethylamine(10 mL) and 2-acetylpyridine (40 mL) was refluxed at 100 °C for 16 h, then concentrated by rotating evaporationto give dark brown solid. This was washed with hexane(100 mL) and diethyl ether (100 mL) to give the pure and bright yellow crystalline product. Hydrazine monohydrate (40 mL) and ethanol (15 mL) were mixed with the previously obtained solid, and the mixture was stirred at 60 °C for 30 min. After cooling, distilled water (75 mL) was added to the solution, which was kept at 0 °C for 24 h to produce a light yellow precipitate. This was recrystallized from a mixture of dichloromethane and hexane.
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  • [ 123-11-5 ]
  • [ 13104-56-8 ]
YieldReaction ConditionsOperation in experiment
45.62%
Stage #1: With potassium hydroxide In ethanol at 20℃; for 0.166667 h;
Stage #2: With ammonium hydroxide In ethanol at 37℃; for 24 h;
General procedure: Synthesis of 4′-(3-methoxyphenyl)-2,2′:6′,2″-terpyridine (3-MeO-Phtpy), 4′-(2-methoxyphenyl)-2,2′:6′,2″-terpyridine (2-MeO-Phtpy) and 4′-(4-methoxyphenyl)-2,2′:6′,2″-terpyridine (4-MeO-Phtpy) were performed using the methods described previously [27–33]. 2-Acetylpyridine (2.813g, 23.2mmol, 2 eq.) was added to 2-methoxybenzaldehyde, 3-methoxybenzaldehyde or 4-methoxybenzaldehyde (11.6mmol, 1 eq.) dissolved in 50mL ethanol. KOH pellets (46.5mmol, 4 eq.) were added to this solution. The reaction mixture was stirred at room temperature for 10min. NH3 (40mL, 25percent aq.) was slowly added to the reaction mixture. After a 24-h incubation at 37°C, 5mL of 25percent aq. NH3 was added to the reaction mixture again. The flask containing the reaction mixture was cooled to−20°C. The obtained white precipitate in the flask was isolated through filtration and washed with cold ethanol. We further purified the each product using recrystallization in ethanol-H2O. After recrystallization, each product was recovered by filtration, washed with cold ethanol and petroleum ether, and dried under high vacuum for 24h (Scheme 1).
37% With ammonium hydroxide; potassium hydroxide In ethanol at 20℃; for 24 h; General procedure: Ketone (20 mmol) (2-acetylpyridine, 2-acetylthiazole or 2-acetylpyrazine)was added to a solution of aldehyde (10 mmol) (4-methoxybenzaldehyde,4-methoxy-1-naphthaldehyde or 6-methoxy-2-naphthaldehyde) in EtOH (75 mL). KOH (1.54 g, 27.5 mmol) and NH3(aq)(35 mL) were then added. The solution was stirred at room temp. for 24 h. The solid was collected by filtration and washed with H2O. Recrystallization from ethanol (L1,L4, L7) or toluene (L2, L3, L5, L6, L8,L9) afforded a crystalline solid. 4′-(4-methoxy-1-phenyl)-2,2′:6′,2″-terpyridine (L1): Yield: 37percent. IR(KBr, cm−1): 1588(s), 1467(m), 1389(m), 1204(m), 1157(m),1069(m), 790(m), 739(m) and 655(m). NMR: 1H NMR (400 MHz,CDCl3) δ 8.73 (d, J=4.1 Hz, 2H, HA1), 8.71 (s, 2H, HB2), 8.67 (d,J=7.9 Hz, 2H, HA4), 7.90–7.85 (m, 4H, HC2+A3), 7.37–7.33 (m, 2H,HA2), 7.03 (d, J=8.7 Hz, 2H, HC3), 3.88 (s, 3H, HC5). 13C NMR(100 MHz, CDCl3) δ 160.66, 156.55, 155.99, 149.90, 149.24, 136.96,130.92, 128.67, 123.87, 121.49, 118.42, 114.46, 55.52. C22H17N3O(339.39 g mol−1): calcd C, 77.86; H, 5.05; N, 12.38percent; found: C, 77.46;H, 5.35; N, 12.25percent. DSC: (I run) Tm=164 °C; (II run) Tg=30, Tc=82and Tm=163 °C.
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YieldReaction ConditionsOperation in experiment
50% With ammonia; sodium hydroxide In ethanol; water at 20℃; for 17 h; Round bottom flask 4-methoxycarbonyl benzaldehyde (1.0g, 6.1mmol) and 2-acetyl pyridine (1.37ml, 12.2mmol) were dissolved in 25ml of ethanol.Then 30percent NH3were placed in a round flask, that the solution (1ml) and NaOH (0.488g, 12.2mmol) was dissolved in a minimal amount of water.Put the clear liquid solution of NaOH runners ttuieotgo is light yellow, and after about an hour and caught the red.In about 17 hours at room temperature, open the entrance to the round bottom flask and stirred haenotgo allow air to enter.Over time, the precipitate produced was more yellow.After the reaction was terminated, and then dissolved into water (50ml) and neutralized with HCl.The precipitate was filtered out and washed with water by filtration.And placed in 50ml of ethanol was refluxed for 1 hour and filtered and dried under vacuum (yield: 50percent).
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