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Product Details of [ 5315-25-3 ]

CAS No. :5315-25-3 MDL No. :MFCD00040743
Formula : C6H6BrN Boiling Point : -
Linear Structure Formula :- InChI Key :SOHDPICLICFSOP-UHFFFAOYSA-N
M.W :172.02 Pubchem ID :79205
Synonyms :

Calculated chemistry of [ 5315-25-3 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.9
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.95
Log Po/w (XLOGP3) : 1.81
Log Po/w (WLOGP) : 2.15
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 2.54
Consensus Log Po/w : 2.01

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.6
Solubility : 0.43 mg/ml ; 0.0025 mol/l
Class : Soluble
Log S (Ali) : -1.7
Solubility : 3.43 mg/ml ; 0.0199 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.26
Solubility : 0.0948 mg/ml ; 0.000551 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 5315-25-3 ]

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 [ 5315-25-3 ]

* 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 [ 5315-25-3 ]
  • Downstream synthetic route of [ 5315-25-3 ]

[ 5315-25-3 ] Synthesis Path-Upstream   1~50

  • 1
  • [ 5315-25-3 ]
  • [ 1824-81-3 ]
YieldReaction ConditionsOperation in experiment
75% With ammonium hydroxide; copper(I) iodide; 1-ethylacetoacetate-3-methyl imidazolium hydroxide In acetonitrile at 80℃; for 12 h; Inert atmosphere General procedure: An oven-dried flask was charged with aryl halide (1.0 mmol), aqueous NH3 (28percent, 1.5 mmol), CuI nanoparticles (0.02 mmol), 4a (3.0 mmol) and acetonitrile (2 mL). The contents were stirred under argon atmosphere at rt for 12 h. After completion of the reaction as monitored by TLC, the product was extracted with diethyl ether (5×5 mL). The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. Purification was done on silica gel column, and elution with ethyl acetate–hexane mixture afforded the aminated products. All products obtained herein are known compounds, and were confirmed by 1H NMR, 13C NMR and mass spectroscopic analysis, see Supplementary data for full details.
Reference: [1] Chemical Communications, 2010, vol. 46, # 6, p. 925 - 927
[2] Tetrahedron, 2013, vol. 69, # 25, p. 5092 - 5097
[3] Tetrahedron Letters, 2008, vol. 49, # 21, p. 3471 - 3474
  • 2
  • [ 5315-25-3 ]
  • [ 107-21-1 ]
  • [ 1824-81-3 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 19, p. 3251 - 3254
  • 3
  • [ 5315-25-3 ]
  • [ 18368-57-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1959, vol. <4> 8, p. 44,46, 48, 50
  • 4
  • [ 1824-81-3 ]
  • [ 5315-25-3 ]
YieldReaction ConditionsOperation in experiment
93.1%
Stage #1: at 60 - 62℃; for 1 h;
Stage #2: at -5 - -3℃; for 3 h;
Stage #3: With sodium nitrite In water for 3 h;
under stirring conditions, the mass concentration in the reaction tank 46percent the hydrobromidum 756g, 2-amino-6-methyl pyridine 108g, heating to 60-62 °C and thermal insulation 1h, then cool to-5 - - 3°C, keep the range of the temperature is dropping 640g bromine Br2, re-insulation 3h; in the range of the temperature is dropping mass concentration of 30percent sodium nitrite aqueous solution 920g, completion of the dropping, without the control of the reaction temperature the stirring reaction 3h; end of the reaction, the reaction solution when the temperature is reduced to 15 °C rear, used for quality concentration 30percent sodium hydroxide aqueous solution to regulate the pH=11, then through steam distillation to obtain 2-bromo-6-methylpyridine 150g, vapor content is 99.4percent, yield of 93.1percent;
80% With hydrogen bromide; bromine; sodium nitrite In water at -20 - 30℃; Example 31; 2-bromopicoline (104); 2-amino-picoline (37.35 g, 0.346 mol) is added to a mechanically-stirred round-bottom flask in several stages, in a hydrobromic acid solution (48percent in water, 187 mL) at a temperature maintained between 20 and 30° C. After entire dissolution of the reagent, the reaction medium is cooled to 20° C. during the dropwise addition of dibromine (49 mL, 0.966 mol), for 30 min. The temperature of the solution is maintained at -20° C. for 90 minutes. In sodium nitrite solution (63.5 g, 6 mol) in water (100 mL) is added dropwise. The temperature of the solution is then brought to 15° C. in an hour and stirred for 45 minutes at that temperature. The medium is cooled to -20° C. and treated with a sodium solution (249 g, 400 mL H2O) at a temperature maintained at below -10° C. during the adding. After return to room temperature, the solution is stirred for an hour and then extracted with AcOEt. The organic phase is dried over Na2SO4, filtered and concentrated under reduced pressure. The residue is distilled under vacuum and the 2-bromopicoline (104) is obtained in the form of a colourless oil with a yield of 80percent.bp 129-132° C. (2.6 mbar).1H RMN (CDCl3) δ (ppm): 2.49 (s, 3H, H7), 7.08 (d, J=7.6, 1H, H5), 7.24 (d, J 7.6, 1H, H3), 7.41 (t, 1H, H4).
72%
Stage #1: at 0℃; for 1.5 h;
Stage #2: With sodium nitrite In water at 10℃; for 2 h;
An alkali trap, an equal pressure dropping funnel, a thermometer, and a mechanical stirrer were attached to a 1000 mL four-necked round bottom flask. (A) 2-amino-6-picoline (27.0 g 0.25 mol) and 48percent HBr (125 mL 2.31 mol) were placed in this reaction vessel. The reaction vessel was immersed in an ice bath and cooled to 0 ° C. Br2 (37.5 mL 0.72 mol) was transferred to an equal pressure dropping funnel, The temperature of the reaction solution was kept at 0 ° C. and slowly dropped into the reaction vessel over 90 minutes while vigorously stirring with a mechanical stirrer. NaNO 2 (42.5 g 0.62 mol) was weighed and dissolved in about 100 mL of distilled water. This was transferred to an equal pressure dropping funnel,While stirring vigorously with a stirrer, it dripped over about 2 hours. At this time, care was taken that the temperature of the reaction solution did not exceed 10 ° C. In order to complete the reaction, NaNO 2 (2.50 g 0.036 mol) was dissolved in about 10 mL of distilled water and added, It was confirmed that nitrogen gas was not generated from the reaction vessel. While cooling in an ice bath, NaOH (95.0 g, 2.4 mol) was dissolved in about 300 mL of distilled water, after cooling sufficiently, it was gradually added to the solution for neutralization. At this time, care was taken that the temperature of the reaction solution did not exceed 20 ° C. The reaction mixture was extracted with Et 2 O (200 mL × 4) and the organic layer was collected. Anhydrous Na 2 SO 4 was added and dried, Upon concentration, a brown oily substance was obtained. This oily substance was distilled under reduced pressure in a rectifying tube, fractionated at 55 ° C. to 60 ° C. at a reduced pressure degree of 7.00 mmHg, A yellow oily substance was obtained. This material was stored at -40 ° C. Yield: 72percent (32.0 g)
66%
Stage #1: at -10 - 0℃; for 2 h;
Stage #2: With sodium nitrite In water for 3 h;
1000 ml Four-neck reaction vessel was equipped with a mechanical stirrer,Alkaline trap,Two 200 ml isobaric dropping funnels were attached,(J) 2-amino-6-picoline (27.0 g 0.25 mol) was added,Was dissolved in 48percent HBr (125 ml 2.31 mol)The mixture was vigorously stirred with a mechanical stirrer.The reaction vessel was immersed in an ice bath containing saline,It was cooled to -10 ° C.The procedure up to neutralization below was done in an ice bath.Br2 (37.5 ml 0.72 mol) was transferred to an isobaric dropping funnel with vigorous stirring with a mechanical stirrer,And slowly added dropwise to the reaction vessel over about 2 hours while maintaining the temperature of the reaction solution at 0 ° C.The solution turned from light yellow to orange to brown.Weigh out NaNO 2 (42.5 g 0.615 mol)It was dissolved in about 100 ml distilled water.This was added dropwise from an isobaric dropping funnel over about 3 hours.At this time,Care was taken that the temperature of the reaction solution did not exceed 10 ° C.In order to complete the reaction,Further, NaNO 2 (2.50 g 0.036 mol) was dissolved in about 10 ml of distilled water and added, and it was confirmed that no bubbles were generated from the reaction solution.While keeping the solution at a low temperature in an ice bath,NaOH (95 g 2.35 mol) was dissolved in about 300 ml of distilled water,After cooling sufficiently,Was added to the solution little by little using an isobaric dropping funnel to neutralize.At this time,Care was taken that the temperature of the reaction solution did not exceed 20 ° C.When the pH became neutral, the color of the solution turned into fluorescent yellow.After checking that the pH reached around 8 with pH test paper, stop the addition, transfer the reaction solution to a separating funnel, extract with Et 2 O (300 ml × 5), collect the organic layer, dry with Na 2 SO 4, Upon concentration, a brown oily substance was obtained.This oily substance was subjected to distillation under reduced pressure (oil bath temperature 55 ° C.) using a distillation apparatus equipped with a rectifying tube to obtain 28.4 g of a transparent yellow oil substance.This material was degassed and purged with nitrogen and then stored at -40 ° C.Yield: 66percent

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[2] Organic Letters, 2000, vol. 2, # 21, p. 3373 - 3376
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2002, vol. 177, # 11, p. 2579 - 2587
[4] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[5] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 19, p. 3151 - 3155
[6] Patent: US2010/4443, 2010, A1, . Location in patent: Page/Page column 33
[7] Tetrahedron Letters, 2006, vol. 47, # 11, p. 1793 - 1796
[8] Inorganic Chemistry, 2018, vol. 57, # 9, p. 5486 - 5498
[9] Dalton Transactions, 2007, # 33, p. 3676 - 3683
[10] Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 9, p. 2237 - 2247
[11] Tetrahedron, 2009, vol. 65, # 36, p. 7673 - 7686
[12] Patent: JP2017/197451, 2017, A, . Location in patent: Paragraph 0029
[13] Patent: JP2017/57177, 2017, A, . Location in patent: Page/Page column 9; 13
[14] Journal of the Chemical Society, 1954, p. 2693,2697
[15] Journal of the American Chemical Society, 1954, vol. 76, p. 3168,3171
[16] Journal of the American Chemical Society, 1951, vol. 73, p. 2109,2112
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[18] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1995, # 9, p. 1511 - 1518
[19] Acta Chemica Scandinavica, 1997, vol. 51, # 4, p. 462 - 469
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[21] Journal of the American Chemical Society, 2004, vol. 126, # 15, p. 4888 - 4896
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[23] Patent: US4338326, 1982, A,
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[27] Asian Journal of Chemistry, 2015, vol. 27, # 11, p. 4141 - 4144
  • 5
  • [ 18368-63-3 ]
  • [ 5315-25-3 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 24, p. 4181 - 4184
  • 6
  • [ 626-05-1 ]
  • [ 74-88-4 ]
  • [ 5315-25-3 ]
Reference: [1] Green Chemistry, 2011, vol. 13, # 5, p. 1110 - 1113
[2] Australian Journal of Chemistry, 2013, vol. 66, # 2, p. 199 - 207
  • 7
  • [ 626-05-1 ]
  • [ 917-54-4 ]
  • [ 5315-25-3 ]
Reference: [1] Acta Chemica Scandinavica, 1996, vol. 50, # 4, p. 316 - 322
  • 8
  • [ 626-05-1 ]
  • [ 77-78-1 ]
  • [ 5315-25-3 ]
Reference: [1] MedChemComm, 2013, vol. 4, # 3, p. 520 - 526
  • 9
  • [ 3279-76-3 ]
  • [ 5315-25-3 ]
  • [ 3430-15-7 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 417,420
  • 10
  • [ 3279-76-3 ]
  • [ 5315-25-3 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 417,420
  • 11
  • [ 109-06-8 ]
  • [ 5315-25-3 ]
Reference: [1] Journal of the Chemical Society, 1954, p. 2693,2697
  • 12
  • [ 5315-25-3 ]
  • [ 127-19-5 ]
  • [ 6940-57-4 ]
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[2] Journal of the American Chemical Society, 1997, vol. 119, # 24, p. 5606 - 5617
[3] Journal of Organic Chemistry, 1998, vol. 63, # 8, p. 2481 - 2487
  • 13
  • [ 5315-25-3 ]
  • [ 67-56-1 ]
  • [ 63071-03-4 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 19, p. 3151 - 3155
  • 14
  • [ 5315-25-3 ]
  • [ 124-41-4 ]
  • [ 63071-03-4 ]
Reference: [1] Journal of the Chemical Society, 1954, p. 2693,2697
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 24, p. 10171 - 10182
  • 15
  • [ 5315-25-3 ]
  • [ 934-60-1 ]
Reference: [1] Chemical communications (Cambridge, England), 2003, # 15, p. 1948 - 1949
  • 16
  • [ 5315-25-3 ]
  • [ 21190-87-4 ]
Reference: [1] Chemistry - A European Journal, 1997, vol. 3, # 1, p. 99 - 104
[2] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[3] Synthesis, 2003, # 4, p. 551 - 554
[4] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 16, p. 1927 - 1934
[5] Tetrahedron Letters, 2001, vol. 42, # 35, p. 6113 - 6115
[6] Patent: WO2006/21801, 2006, A1, . Location in patent: Page/Page column 43
[7] Patent: US6251925, 2001, B1,
  • 17
  • [ 5315-25-3 ]
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 13602-11-4 ]
Reference: [1] Chemical communications (Cambridge, England), 2003, # 15, p. 1948 - 1949
  • 18
  • [ 5315-25-3 ]
  • [ 13602-11-4 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 9, p. 2930 - 2934
  • 19
  • [ 3279-76-3 ]
  • [ 5315-25-3 ]
  • [ 3430-15-7 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 417,420
  • 20
  • [ 5315-25-3 ]
  • [ 5315-24-2 ]
Reference: [1] Patent: US2008/90861, 2008, A1, . Location in patent: Page/Page column 16
  • 21
  • [ 5315-25-3 ]
  • [ 21190-88-5 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 35, p. 6113 - 6115
[2] Chemistry - A European Journal, 1997, vol. 3, # 1, p. 99 - 104
  • 22
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  • [ 2402-78-0 ]
  • [ 366-18-7 ]
  • [ 4411-80-7 ]
  • [ 57154-73-1 ]
  • [ 33777-92-3 ]
  • [ 56100-22-2 ]
YieldReaction ConditionsOperation in experiment
47% With [Ni(2,2'-bipyridine)2Br2]; sodium iodide In N,N-dimethyl-formamide at 20℃; for 8 h; Electrochemical reaction; Inert atmosphere General procedure: To an undivided electrochemical cell, fitted by a zinc rod as the anode and surrounded by a nickel foam as the cathode, were added DMF (50 mL), 0.1 M NaI, and 1,2-dibromoethane (2.5 mmol, 215 μL). The mixture was electrolyzed under argon at a constant current intensity of 0.2 A at room temperature for 20 min. Then the current was stopped, and [Ni(bpy)]Br2 complex21 (2.6 mmol, 562 mg), 2,6-dichloropyridine (5 mmol, 0.74 g), and 2-bromo-6-methylpyridine (10 mmol, 1.72 g) were sequentially added. The solution was electrolyzed at 0.1 A and room temperature until the starting material was totally consumed (8 h).
Reference: [1] Tetrahedron, 2012, vol. 68, # 10, p. 2383 - 2390
  • 23
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  • [ 56100-22-2 ]
Reference: [1] Synlett, 2003, # 6, p. 852 - 854
[2] Tetrahedron Letters, 2009, vol. 50, # 38, p. 5329 - 5331
[3] Tetrahedron, 2010, vol. 66, # 17, p. 3135 - 3146
  • 24
  • [ 5315-25-3 ]
  • [ 2402-78-0 ]
  • [ 4411-80-7 ]
  • [ 1170693-78-3 ]
  • [ 33777-92-3 ]
  • [ 56100-22-2 ]
YieldReaction ConditionsOperation in experiment
10% With nickel(II) bromide hydrate; sodium iodide In N,N-dimethyl-formamide at 20℃; for 8 h; Electrochemical reaction; Inert atmosphere General procedure: To an undivided electrochemical cell, fitted by a zinc rod as the anode and surrounded by a nickel foam as the cathode, were added DMF (50 mL), 0.1 M NaI, and 1,2-dibromoethane (2.5 mmol, 215 μL). The mixture was electrolyzed under argon at a constant current intensity of 0.2 A at room temperature for 20 min. Then the current was stopped, and [Ni(bpy)]Br2 complex21 (2.6 mmol, 562 mg), 2,6-dichloropyridine (5 mmol, 0.74 g), and 2-bromo-6-methylpyridine (10 mmol, 1.72 g) were sequentially added. The solution was electrolyzed at 0.1 A and room temperature until the starting material was totally consumed (8 h).
Reference: [1] Tetrahedron, 2012, vol. 68, # 10, p. 2383 - 2390
  • 25
  • [ 109-04-6 ]
  • [ 5315-25-3 ]
  • [ 366-18-7 ]
  • [ 4411-80-7 ]
  • [ 56100-22-2 ]
YieldReaction ConditionsOperation in experiment
56 %Chromat. With nickel(II) bromide hydrate; sodium iodide In N,N-dimethyl-formamide at 20℃; Electrochemical reaction; Inert atmosphere General procedure: The controlled current preparative electrolysis were carried out with a potentiostat/galvanostat equipment. Undivided cells with 20 mL compartment were used. Zn or Fe metallic rod with 8 mm diameter was used as the sacrificial anode. Ni foam (6 cm.x.3.5 cm) was used as the cathode. It could be re-used after washing with a 6 M HCl solution following by water and acetone, and dried. The same solution was used to clean the anode. A 5 mL DMF solution containing 7percent or 20percent of NiBr2*xH2O or [Ni(bpy)]Br221 and x mmol of the corresponding mixture of 2-bromomethylpyridines or 2,6-dihalopyridines (heterocouplings in Table 1, Table 2, Table 4 and Table 5), or (2.5 mmol) of 2,6-dihalopyridines (homocoupling in Table 3) was stirred or sonicated before the electrolysis, to ensure the solubilization of reagents. A pre-electrolysis was carried out with 15 mL of the electrolytic solution (DMF, 0.1 M NaI and 0.75 mmol of 1,2-dibromoethane), passing a charge of 146 C (I=150 mA). Then, the previous prepared solution of bromopicoline or bromopyridine and the catalyst in 5 mL DMF, was added to the electrolytic cell and the constant current electrolysis (I=100 mA) applied. It is important to ensure that the cell potential must not exceed 1.8 V in order to avoid the reduction of the substrate on the cathode surface. After the total consumption of the reagent (number of coulombs described in the tables), the reaction was stopped and the solvent removed under reduced pressure. The residue was dissolved in CH2Cl2 and washed with several portions of a 6 M NH4OH solution. After drying over Na2SO4, the organic layer was evaporated under reduced pressure.
Reference: [1] Tetrahedron, 2012, vol. 68, # 10, p. 2383 - 2390
  • 26
  • [ 5315-25-3 ]
  • [ 2402-78-0 ]
  • [ 366-18-7 ]
  • [ 4411-80-7 ]
  • [ 1170693-78-3 ]
  • [ 57154-73-1 ]
  • [ 33777-92-3 ]
  • [ 56100-22-2 ]
YieldReaction ConditionsOperation in experiment
16% With [Ni(2,2'-bipyridine)2Br2]; sodium iodide In N,N-dimethyl-formamide at 20℃; for 8 h; Electrochemical reaction; Inert atmosphere General procedure: To an undivided electrochemical cell, fitted by a zinc rod as the anode and surrounded by a nickel foam as the cathode, were added DMF (50 mL), 0.1 M NaI, and 1,2-dibromoethane (2.5 mmol, 215 μL). The mixture was electrolyzed under argon at a constant current intensity of 0.2 A at room temperature for 20 min. Then the current was stopped, and [Ni(bpy)]Br2 complex21 (2.6 mmol, 562 mg), 2,6-dichloropyridine (5 mmol, 0.74 g), and 2-bromo-6-methylpyridine (10 mmol, 1.72 g) were sequentially added. The solution was electrolyzed at 0.1 A and room temperature until the starting material was totally consumed (8 h).
Reference: [1] Tetrahedron, 2012, vol. 68, # 10, p. 2383 - 2390
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  • [ 17997-47-6 ]
  • [ 56100-22-2 ]
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  • 28
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  • [ 882521-96-2 ]
  • [ 56100-22-2 ]
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  • 29
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  • [ 56100-22-2 ]
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  • 30
  • [ 5315-25-3 ]
  • [ 87905-04-2 ]
  • [ 56100-22-2 ]
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  • 31
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  • [ 21948-75-4 ]
  • [ 56100-22-2 ]
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  • 32
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  • [ 34160-40-2 ]
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  • 33
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  • [ 62674-71-9 ]
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  • [ 75-36-5 ]
  • [ 62674-71-9 ]
YieldReaction ConditionsOperation in experiment
94% With sodium iodide In acetonitrile Preparation 9
2-Iodo-6-methylpyridine (10b)
To a solution of 2-bromo-6-methylpyridine (2.0 g, 11.6 mmol) and sodium iodide (2.78 g, 18.6 mmol) in dry acetonitrile (13 mL) was added acetyl chloride (1.9 g, 24.4 mmol) dropwise, and the resulting light yellow suspension was heated to reflux. G.C. analysis after 16 hours at reflux indicated only 50percent conversion.
Added additional acetyl chloride (1 equivalent) and sodium iodide (0.8 equivalent) and refluxed for 16 hours. G.C. analysis indicated 90percent conversion to desired product in addition to the expected bromo and chloro by-products.
The reaction was cooled to room temperature, diluted with aqueous potassium carbonate and sodium bisulfite (75 mL, 10 and 5percent respectively), and extracted with diethyl ether (2*75 mL).
The organics were combined, washed with the carbonate/bisulfite solution, dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure to give 2.39 g (94percent) of crude product as a dark oil.
Used without further purification. 1H NMR (CDCl3) δ2.52 (s, 3H,), 7.10 (d, 1H, J=7.51 Hz), 7.20 (t, 1H, J=7.69 Hz, J=7.51 Hz), 7.58 (d, 1H, J=7.69 Hz).
(Tetrahedron Lett. 1990, 31, 6757)
Reference: [1] Patent: US2002/19370, 2002, A1,
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  • [ 83004-10-8 ]
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[4] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 17, p. 5071 - 5074
[5] Organic and Biomolecular Chemistry, 2009, vol. 7, # 24, p. 5074 - 5077
[6] Organometallics, 2014, vol. 33, # 10, p. 2575 - 2582
[7] Patent: WO2004/14902, 2004, A2, . Location in patent: Page 61-62
[8] Patent: US2004/58970, 2004, A1, . Location in patent: Page 12
  • 36
  • [ 5315-25-3 ]
  • [ 83004-10-8 ]
  • [ 82315-66-0 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 9, p. 1697 - 1700
[2] Tetrahedron Letters, 2002, vol. 43, # 9, p. 1697 - 1700
[3] Synthesis, 1992, # 6, p. 519 - 521
[4] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 22, p. 3737 - 3745
  • 37
  • [ 5315-25-3 ]
  • [ 1692-25-7 ]
  • [ 78210-78-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 224 - 239
  • 38
  • [ 5315-25-3 ]
  • [ 126717-59-7 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 19, p. 3151 - 3155
  • 39
  • [ 5315-25-3 ]
  • [ 131747-53-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
  • 40
  • [ 5315-25-3 ]
  • [ 131747-42-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
  • 41
  • [ 5315-25-3 ]
  • [ 74-88-4 ]
  • [ 83004-13-1 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.616667 h; Inert atmosphere; Cooling with acetone-dry ice
Stage #2: at -78 - 20℃; for 2.5 h; Inert atmosphere; Cooling with acetone-dry ice
Preparation 23
Synthesis of 2-bromo-6-ethyl-pyridine
Add under nitrogen a solution of 2.5 M n-butyllithium in hexanes (186.74 mL, 0.467 mol) over 41 min to a solution of diisopropylamine (68.7 mL, 0.488 mol) in tetrahydrofuran (745 mL, 9.16 mol) at -78° C. (dry-ice/acetone bath).
Stir for 15 min and add 2-bromo-6-methylpyridine (49.3 mL, 0.424 mol) dropwise over 22 min.
Stir 15 min, add methyl iodide (52.87 mL, 0.848 mol) dropwise over 1 hour and then warm to room temperature over 1.5 hour.
Add water (250 mL) while cooling with a dry-ice/acetone bath and separate the layers.
Extract the aqueous phase twice with ethyl acetate (300 mL).
Combine the organic phases, concentrate and purify by silica gel chromatography, gradient eluding from 100:0 to 80:20 using hexanes:ethyl acetate, to give the title compound as a yellow oil (59.74 g, 75percent).
1H NMR (CDCl3) δ 1.28 (t, 3H), 2.80 (q, 2H), 7.11 (d, 1H), 7.27 (d, 1H), 7.45 (t, 1H).
46%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at 20℃; for 3 h;
To a solution of 2-bromo-6-methylpyridine (CAS 5315-25-3) (2.0 g, 11.7 mmol, 1.0 eq) in THF (10 mL) was added LDA (12.3 mL, 12.3 mmol, 1.05 eq) at -78 °C. After stirring at -78 °C for 1 h, CH3I (1.8 g, 12.3 mmol, 1.05 eq) was added to the mixture. The mixture was stirred at rt for 3 h. The mixture was quenched with sat. NH4C1 (2 mL), diluted with water (50 mL) and extracted with EA (2 x 100 mL). The combined organic phase was washed with brine and dried over Na2S04. After concentration, the residue was purified by silica gel chromatography with PE/EA (20/1) as eluent to give 2-bromo-6-ethylpyridine. 1.0 g, as a yellow solid, Y: 46percent. ESI-MS (M+H)+: 185.9, 187.9.
46%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at 20℃; for 3 h;
To a solution of 2-bromo-6-methylpyridine (CAS 53 15-25-3) (2.0 g, 11.7 mmol, 1.0 eq) in THF (10 mL) was added LDA (12.3 mL, 12.3 mmol, 1.05 eq) at -78 °C. After stirring at -78°C for 1 h, CH3I (1.8 g, 12.3 mmol, 1.05 eq) was added to the mixture. The mixture was stirred atrt for 3 h. The mixture was quenched with sat. NH4C1 (2 mL), diluted with water (50 mL) and extracted with EA (2 x 100 mL). The combined organic phase was washed with brine and dried over Na2504. After concentration, the residue was purified by silica gel chromatography with PE/EA (20/1) as eluent to give 2-bromo-6-ethylpyridine. 1.0 g, as a yellow solid, Y: 46percent. ESIMS (M+H): 185.9, 187.9.
Reference: [1] Patent: US2009/253750, 2009, A1, . Location in patent: Page/Page column 9
[2] Patent: WO2016/11390, 2016, A1, . Location in patent: Page/Page column 194
[3] Patent: WO2017/127430, 2017, A1, . Location in patent: Page/Page column 52
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 3, p. 501 - 507
  • 42
  • [ 5315-25-3 ]
  • [ 79055-59-7 ]
Reference: [1] Patent: EP2768509, 2017, B1,
[2] Patent: WO2013/59587, 2013, A1,
  • 43
  • [ 5315-25-3 ]
  • [ 68-12-2 ]
  • [ 955370-07-7 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.833333 h;
Stage #2: at -78℃; for 0.5 h;
Stage #3: With methanol; sodium tetrahydroborate; acetic acid In tetrahydrofuran at -78℃;
Step GA solution of LDA was prepared by adding a 1.6 M solution of n-butyllithium in hexane (51 mL, 81.2 mmol) at 0° C. to a stirred solution of N,N'-diisopropylamine (13.5 mL, 97.4 mmol) in tetrahydrofuran (60 mL). The mixture was stirred at 0° C. for 15 min and then added at -78° C. to a solution of commercially available 2-bromo-6-methyl-pyridine (5 g, 29.1 mmol) in tetrahydrofuran (90 mL). The mixture was stirred at -78° C. for 25 minutes and then N,N'-dimethylformamide (7.9 mL, 107 mmol) was added. After 30 minutes at -78° C., methanol (80 mL) and acetic acid (6.1 mL, 132 mmol) were added. Then sodium borohydride (1.1 g, 28 mmol) was added at -78° C. and the mixture was stirred overnight and allowed to reach room temperature. The reaction mixture was diluted with ethylacetate (150 mL) and washed with a 10percent citric acid solution (80 mL) and brine (80 mL). The organic phase was separated and the aqueous phase extracted with ethylacetate (2.x.150 mL). The combined organic phase was dried over Na2SO4, filtered and the solvents were removed. The residue was purified by chromatography on silica using dichloromethane/acetone (95/5) to afford the title compound as pale yellow oil (5 g, 85percent).1H-NMR (400 MHz, CDCl3): δ=3.01 (t, 2H), 3.09 (t, 1H), 4.02 (q, 2H), 7.16 (d, 1H), 7.34 (d, 1H), 7.43 (t, 1H)
85%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.416667 h;
Stage #2: at -78℃; for 0.5 h;
Stage #3: With methanol; sodium tetrahydroborate; acetic acid In tetrahydrofuran; hexane at -78 - 20℃;
Step G; A solution of LDA was prepared by adding a 1.6 M solution of n-butyllithium in hexane (51 mL, 81.2 mmol) at 0 °C to a stirred solution of N,N'-diisopropylamine (13.5 mL, 97.4 mmol) in tetrahydrofuran (60 mL). The mixture was stirred at 0 °C for 15 min and then added at -78 °C to a solution of commercially available 2-bromo-6-methyl-pyridine (5 g, 29.1 mmol) in tetrahydrofuran (90 mL). The mixture was stirred at -78 °C for 25 minutes and then N,N'-dimethylformamide (7.9 mL, 107 mmol) was added. After 30 minutes at -78 °C, methanol (80 mL) and acetic acid (6.1 mL, 132 mmol) were added. Then sodium borohydride (1.1 g, 28 mmol) was added at -78 °C and the mixture was stirred overnight and allowed to reach room temperature. The reaction mixture was diluted with ethylacetate (150 mL) and washed with a 10 percent citric acid solution (80 mL) and brine (80 mL). The organic phase was separated and the aqueous phase extracted with ethylacetate (2 x 150 mL). The combined organic phase was dried over Na2SO4, filtered and the solvents were removed. The residue was purified by chromatography on silica using dichloromethane/acetone (95/5) to afford the title compound as pale yellow oil (5 g, 85 percent). 1H-NMR (400 MHz, CDCl3): d = 3,01 (t, 2H), 3.09 (t, 1H), 4.02 (q, 2H), 7.16 (d, 1H), 7.34 (d, 1H), 7.43 (t, 1H)
85%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.416667 h;
Stage #2: at -78℃; for 0.5 h;
Stage #3: With methanol; sodium tetrahydroborate; acetic acid In tetrahydrofuran; hexane at -78 - 20℃;
A solution of LDA was prepared by adding a 1.6 M solution of n-butyllithium in hexane (51 mL, 81.2 mmol) at 0 °C to a stirred solution of N,N'-diisopropylamine (13.5 mL, 97.4 mmol) in tetrahydrofuran (60 mL). The mixture was stirred at 0 °C for 15 min and then added at -78 °C to a solution of commercially available 2-bromo-6-methyl-pyridine (5 g, 29.1 mmol) in tetrahydrofuran (90 mL). The mixture was stirred at -78 °C for 25 minutes and then Ν,Ν'- dimethylformamide (7.9 mL, 107 mmol) was added. After 30 minutes at -78 °C, methanol (80 mL) and acetic acid (6.1 mL, 132 mmol) were added. Then sodium borohydride ( 1.1 g, 28 mmol) was added at -78 °C and the mixture was stirred overnight and allowed to reach room temperature. The reaction mixture was diluted with ethylacetate (150 mL) and washed with a 10 percent citric acid solution (80 mL) and brine (80 mL). The organic phase was separated and the aqueous phase extracted with ethylacetate (2 x 150 mL). The combined organic phase was dried over Na2S04, filtered and the solvents were removed. The residue was purified by chromatography on silica using dichloromethane/acetone (95/5) to afford the title compound as pale yellow oil (5 g, 85 percent).-NMR (400 MHz, CDC13): d = 3.01 (t, 2H), 3.09 (t, 1H). 4.02 (q, 211), 7.16 (d, 1H). 7.34 (d, 1 H) 7.43 (t, 1 H)
76.5%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere
Stage #2: at -78℃; for 1 h; Inert atmosphere
To a stirred solution of n-butyllithium (1 L, 1 .6 M in hexane) in tetrahydrofuran was added diisopropylamine (600 mL) dropwise through a dropping funnel at -10 °C under an N2 atmosphere for 30 minutes. The ice bath was removed and the reaction mixture was cooled to -78 °C. A solution of 2-bromo-6-methyl pyridine (100 g, 0.58 mol) in THF ( .6 L) was added and the color changed pale yellow to dark brown. The mixture was stirred for 1 hour at the same temperature and then Λ/,Λ/'-dimethylformamide (200 mL, 2.147 mol) was added. After 60 minutes at -78 °C, methanol (1.6 L) and acetic acid (160 mL, 2.49 mol) were added. Then sodium borohydride (28 g, 0.557 mol) was added at -78 °C and the mixture was allowed to come to room temperature and was stirred overnight. The color changed dark brown to yellow color. The reaction mixture was diluted with ethyl acetate (3.0 L) and 10percent citric acid solution (1.5 L) and was extracted with EtOAc (2 x 2L), and washed with brine (1 L). The combined organic extracts were dried over Na2S04 and solvents were removed under reduced pressure. The residue was purified by column chromatography on silica gel (60-120 mesh) using ethyl acetate/n-heptane (30/70) to afford the title compound as a pale yellow oil (90 g, 76.5percent). 1H-NMR (400 MHz, CDCI3): δ = 7.43 (t, 1 H), 7.34 (d, 1 H), 7.16 (d, 1 H), 4.02 (q, 2H), 3.09 (t, 1 H), 3.01 (t, 2H)

Reference: [1] Patent: US2011/92537, 2011, A1, . Location in patent: Page/Page column 25-26
[2] Patent: EP2311823, 2011, A1, . Location in patent: Page/Page column 26; 28
[3] Patent: WO2011/45383, 2011, A2, . Location in patent: Page/Page column 56
[4] Patent: WO2015/110263, 2015, A1, . Location in patent: Page/Page column 198
  • 44
  • [ 5315-25-3 ]
  • [ 64-19-7 ]
  • [ 955370-07-7 ]
YieldReaction ConditionsOperation in experiment
76.5%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane; N,N-dimethyl-formamide at -78 - -10℃; for 1 h; Inert atmosphere
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide at -78 - 20℃; Inert atmosphere
Preparative Example 65 (0977) (0978) Step A (0979) To a stirred solution of n-butyllithium (1 L, 1.6 M in hexane) in tetrahydrofuran was added diisopropylamine (600 mL) dropwise through a dropping funnel at −10° C. under an N2 atmosphere for 30 minutes. The ice bath was removed and the reaction mixture was cooled to −78° C. A solution of 2-bromo-6-methyl pyridine (100 g, 0.58 mol) in THF (1.6 L) was added and the color changed pale yellow to dark brown. The mixture was stirred for 1 hour at the same temperature and then N,N′-dimethylformamide (200 mL, 2.147 mol) was added. After 60 minutes at −78° C., methanol (1.6 L) and acetic acid (160 mL, 2.49 mol) were added. Then sodium borohydride (28 g, 0.557 mol) was added at −78° C. and the mixture was allowed to come to room temperature and was stirred overnight. The color changed dark brown to yellow color. The reaction mixture was diluted with ethyl acetate (3.0 L) and 10percent citric acid solution (1.5 L) and was extracted with EtOAc (2×2 L), and washed with brine (1 L). The combined organic extracts were dried over Na2SO4 and solvents were removed under reduced pressure. The residue was purified by column chromatography on silica gel (60-120 mesh) using ethyl acetate/n-heptane (30/70) to afford the title compound as a pale yellow oil (90 g, 76.5percent). (0980) 1H-NMR (400 MHz, CDCl3): δ=7.43 (t, 1H), 7.34 (d, 1H), 7.16 (d, 1H), 4.02 (q, 2H), 3.09 (t, 1H), 3.01 (t, 2H)
Reference: [1] Patent: US2017/2005, 2017, A1, . Location in patent: Paragraph 0977; 0978; 0979; 0980
  • 45
  • [ 5315-25-3 ]
  • [ 727356-19-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4721 - 4734
  • 46
  • [ 5315-25-3 ]
  • [ 67-64-1 ]
  • [ 955369-59-2 ]
Reference: [1] Patent: US2007/254892, 2007, A1, . Location in patent: Page/Page column 56
  • 47
  • [ 5315-25-3 ]
  • [ 1093879-46-9 ]
Reference: [1] Patent: US2012/184539, 2012, A1,
[2] Patent: WO2018/106636, 2018, A1,
[3] Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 9088 - 9095
  • 48
  • [ 5315-25-3 ]
  • [ 105-58-8 ]
  • [ 955369-63-8 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -70℃; for 0.5 h;
Stage #2: at -70 - 20℃; for 4 h;
To a solution of 2-bromo-6-methyl-pyridine (5.00 g, 29.0 mmol, CAS 5315-25-3) in THF (100 mL) was added LDA (2.0 M, 30.5 mL) at -70 °C. After 0.5 hour of stirring at -70 °C, diethyl carbonate (5.26 mL, 43.6 mmol) was added. The reaction mixture was slowly warmed to 20 °C and stirred at 20 °C for 4 hours. On completion, the reaction mixture was washed with water (120 mL) and extracted with ethyl acetate (3 X 150 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep- column chromatography (petroleum ether:ethyl acetate = 10:1) to give the title compound (5.50 g, 77percent yield) as a yellowish oil.1H NMR (400MHz, CDCl3) δ = 7.50 - 7.41 (m, 1H), 7.33 (d, J = 7.6 Hz, 1H), 7.21 (d, J = 7.6 Hz, 1H), 4.11 (q, J = 7.2 Hz, 2H), 3.75 (s, 2H), 1.20 (t, J = 7.2 Hz, 3H).
55%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #2: at -78 - 20℃;
To a solution of N,N-diisopropylamine (1.85 g, 18.31 mmol) in anhydrous THF (7 mL) cooled to −78° C., a solution of n-butyllithium (2.5 M in hexane, 17.44 mmol) was added drop wise under inert atmosphere. The mixture was stirred at −78° C. for one hour and then 2-bromo-6-methylpyridine (1.5 g, 8.7 mmol). The reaction mixture was stirred at −78° C. for one hour and a solution of diethyl carbonate (1.23 g, 10.46 mmol) in THF (3 mL) was added. The reaction mixture was allowed to warm up to room temperature and left stirring overnight. The mixture was quenched with H2O and extracted twice with AcOEt. The organic layer was collected, washed with saturated sodium chloride solution, dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (cHex/AcOEt 70/30) to give the title compound as an yellow oil (1.16 g, 55percent). (0362) C9H10BrNO2 Mass (calculated) [244]; (found) [M+H]+=246.
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 9088 - 9095
[2] Patent: WO2018/106636, 2018, A1, . Location in patent: Paragraph 00238
[3] Patent: US2016/297762, 2016, A1, . Location in patent: Paragraph 0361-0362
  • 49
  • [ 5315-25-3 ]
  • [ 108-18-9 ]
  • [ 105-58-8 ]
  • [ 955369-63-8 ]
Reference: [1] Patent: EP2878339, 2015, A1, . Location in patent: Page/Page column
  • 50
  • [ 5315-25-3 ]
  • [ 955369-63-8 ]
Reference: [1] Patent: US2012/184539, 2012, A1,
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