Home Cart Sign in  
Chemical Structure| 5315-25-3 Chemical Structure| 5315-25-3

Structure of 5315-25-3

Chemical Structure| 5315-25-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 5315-25-3 ]

CAS No. :5315-25-3
Formula : C6H6BrN
M.W : 172.02
SMILES Code : C1=C(N=C(C=C1)Br)C
MDL No. :MFCD00040743
InChI Key :SOHDPICLICFSOP-UHFFFAOYSA-N
Pubchem ID :79205

Safety of [ 5315-25-3 ]

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

Computational Chemistry of [ 5315-25-3 ] Show Less

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 ?

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

12.89 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.95
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

1.81
Log Po/w (WLOGP)?

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

2.15
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.

1.58
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

2.54
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.01

Water Solubility

Log S (ESOL):?

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

-2.6
Solubility 0.43 mg/ml ; 0.0025 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.7
Solubility 3.43 mg/ml ; 0.0199 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

-3.26
Solubility 0.0948 mg/ml ; 0.000551 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

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.06 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

2.0
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)

1.64

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.

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

[ 5315-25-3 ] Synthesis Path-Downstream   1~24

  • 1
  • [ 5315-25-3 ]
  • [ 2314-97-8 ]
  • [ 1620-72-0 ]
  • 2
  • [ 5315-25-3 ]
  • [ 1066-54-2 ]
  • [ 30413-58-2 ]
YieldReaction ConditionsOperation in experiment
24% 2-bromo-6-methylpyridine (0.5 g, 2.9 mmol) and trimethylsilylacetylene (0.29 g, 2.9 mmol) in Et3N (15 ml) is purged with argon. Then CuI (11 mg, 0.06 mmol) and (PPh3)2PdCl2 (42 mg, 0.06 mmol) are added and the reaction stirred under argon at room temp for 2 hours. The solvent is removed in vacuo and the residue diluted in EtOAc (50 ml) and water (50 ml). The organic is separated and washed with brine. The solvent is removed to afford a dark oil. This oil is diluted in MeOH (50 ml) and treated with a 1 N NaOH solution (10 ml) and stirred for 3 hours at room temp. The aqueous is then acidified to pH=4 with 1 N HCl and extracted with dichloromethane. The solvent is removed in vacuo to afford 1.16 g (24 %) as a light yellow oil used as is in following reactions. 1H NMR (CDCl3) delta: 7.54 (t, 1H), 7.29 (d, 1H), 7.12 (d, 1H), 3.12 (s, 1H), 2.55 (s, lH).MS ES+ m/e 118.1 (M+1)
  • 3
  • [ 5315-25-3 ]
  • [ 74-88-4 ]
  • [ 83004-13-1 ]
YieldReaction ConditionsOperation in experiment
75% 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) delta 1.28 (t, 3H), 2.80 (q, 2H), 7.11 (d, 1H), 7.27 (d, 1H), 7.45 (t, 1H).
46% 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% 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.
  • 7
  • [ 5315-25-3 ]
  • [ 131747-53-0 ]
  • 8
  • [ 5315-25-3 ]
  • [ 75-36-5 ]
  • [ 62674-71-9 ]
YieldReaction ConditionsOperation in experiment
2.39 g (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) delta2.52 (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)
  • 9
  • [ 1455-20-5 ]
  • [ 5315-25-3 ]
  • [ 4411-80-7 ]
  • [ 1062177-17-6 ]
  • 10
  • [ 5315-25-3 ]
  • [ 68-12-2 ]
  • [ 955370-07-7 ]
YieldReaction ConditionsOperation in experiment
85% 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 10% citric acid solution (80 mL) and brine (80 mL). The organic phase was separated and the aqueous phase extracted with ethylacetate (2×150 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%).1H-NMR (400 MHz, CDCl3): delta=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% 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 % 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 %). 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% 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 Nu,Nu'- 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 % 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 %).-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% 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 Lambda/,Lambda/'-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 10% 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, 76.5%). 1H-NMR (400 MHz, CDCI3): delta = 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)

  • 11
  • [ 5315-25-3 ]
  • [ 870119-58-7 ]
  • [ 1360431-90-8 ]
  • 12
  • [ 5315-25-3 ]
  • [ 5932-27-4 ]
  • [ 930087-23-3 ]
YieldReaction ConditionsOperation in experiment
54% With copper(l) iodide; potassium carbonate; trans-1,2-cyclohexanediamine; In 1,4-dioxane; for 48h;Reflux; Inert atmosphere; To a mixture of 3-(ethoxycarbonyl)pyrazole (1 g, 7.14 mmol), CuI (1.12 g, 5.88 mmol) and K2CO3 (1.97 g, 14.29 mmol) in dioxane (20 mL) was added 2-bromo-6-methylpyridine (1.02 g, 5.96 mmol) and trans-1,2-cyclohexanediamine (0.68 g, 5.96 mmol). The mixture was heated at reflux under an atmosphere of argon for 48 h, after which it was cooled to room temperature, diluted with ethyl acetate (80 mL) and filtered through a plug of Celite. The filtrate was washed with saturated EDTA aqueous solution (2 * 25 mL) and was then dried with Na2SO4. The solvents were evaporated under reduced pressure, and the residue was purified by column chromatography (silica, CH2Cl2 as eluent) to give desired product 1 (739 mg, 54percent) as a yellow oil. Rf (CH2Cl2-petroleum ether, 98:02) = 0.50. IR (NaCl plates): nu 1738 cm-1 (CO ester). 1H NMR (CDCl3): delta 1.37 (3H, t, J = 6 Hz), 2.51 (3H, s), 4.39 (2H, q, J = 6 Hz), 6.90 (1H, d, J = 3 Hz), 7.04 (1H, d, J = 9 Hz), 7.66 (1H, t, J = 9 Hz), 7.86 (1H, d, J = 9 Hz), 8.57 (1H, d, J = 3 Hz). 13C NMR (CDCl3): delta 14.35 (CH3), 24.2 (CH3), 61.2 (CH2), 109.85 (CH), 110.0 (CH), 121.9 (CH), 128.3 (CH), 138.9 (CH), 145.7 (Cq), 150.3 (Cq), 157.5 (Cq), 162.3 (CO). MS (ESI+): m/z (percent) 270 (49) [M+K]+, 254 (100) [M+Na]+, 232 (36) [M+H]+.
  • 13
  • [ 5315-25-3 ]
  • [ 77152-08-0 ]
  • [ 1620-72-0 ]
  • 14
  • [ 5315-25-3 ]
  • (1,10-phenanthroline)(trifluoromethyl)copper(I) [ No CAS ]
  • [ 1620-72-0 ]
  • 15
  • [ 5315-25-3 ]
  • [ 4775-98-8 ]
  • 16
  • [ 5315-25-3 ]
  • [ 1679-18-1 ]
  • [ 61704-26-5 ]
YieldReaction ConditionsOperation in experiment
99% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 70 - 90℃; for 18h;Inert atmosphere; A stream of argon, 2-bromo-6-methyl-pyridine (30.2g, 0.18mol), 4- chlorophenyl boronic acid (21.1g, 0.13mol), and tetrakis (triphenylphosphine) palladium (3.12g, 2.7 mmol) was suspended in 1,4-dioxane (340 mL), was heated to 70 C.. After dropping slowly 1.0M- aqueous potassium carbonate solution (405mL) to this, the temperature was raised to 90 , and the mixture was stirred for 18 hours. After cooling, was separated with chloroform, the organic layer was concentrated, the resulting crude product was purified by silica gel chromatography purification (developing solvent chloroform: hexane = 1 1 (by volume ratio, the same hereinafter)), to obtain the desired product of 2- (4-chlorophenyl) -6-methyl pyridine of yellow crystals (yield 27.0g, 99% yield).
  • 17
  • [ 5315-25-3 ]
  • [ 64-19-7 ]
  • [ 955370-07-7 ]
YieldReaction ConditionsOperation in experiment
76.5% 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 10% 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, 76.5%). (0980) 1H-NMR (400 MHz, CDCl3): delta=7.43 (t, 1H), 7.34 (d, 1H), 7.16 (d, 1H), 4.02 (q, 2H), 3.09 (t, 1H), 3.01 (t, 2H)
  • 18
  • [ 5315-25-3 ]
  • [ 175883-62-2 ]
  • C14H15NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.2 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; for 16h;Reflux; Reference Production Example 5 (0110) A mixture of 1.93 g of <strong>[175883-62-2]4-methoxy-3-methylphenylboronic acid</strong>, 2.00 g of 2-bromo-5-methylpyridine, 0.48 g of [1,1?-bis(diphenylphosphino)ferrocene] palladium(II) dichloride dichloromethane adduct, 4.20 g of sodium carbonate, 20 ml of 1,4-dioxane and 1 ml of water was heated to reflux for 16 hours. After being cooled, the reaction mixture was filtered, and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and was dried over anhydrous sodium sulfate, followed by being condensed under reduced pressure. The result residue was subjected to silica gel column chromatography to give 2.20 g of Intermediate (21A) represented by the following formula. 1H-NMR (CDCl3) delta: 2.29 (3H, s), 2.61 (3H, s), 3.87 (3H, s), 6.89 (1H, d), 7.02 (1H, d), 7.45 (1H, d), 7.58 (1H, t), 7.77 (1H, dd), 7.80 (1H, s).
  • 20
  • [ 5315-25-3 ]
  • [ 115-19-5 ]
  • [ 30413-58-2 ]
  • 21
  • [ 5315-25-3 ]
  • [ 15016-42-9 ]
  • 2-methyl-6-(2-vinylphenyl)pyridine [ No CAS ]
  • 22
  • [ 5315-25-3 ]
  • [ 15016-42-9 ]
  • 4,7-dimethyl-6H-pyrido[2,1-a]isoquinolin-6-one [ No CAS ]
  • 23
  • [ 5315-25-3 ]
  • [ 15754-51-5 ]
  • bis(4-methoxyphenyl)(6-methylpyridin-2-yl)phosphine oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With bis(triphenylphosphine)nickel(II) chloride; potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 24h;Schlenk technique; Inert atmosphere; Add bis(p-methoxyphenyl) phosphorus oxide (0.952g, 5mmol), 2-bromo-6-methylpyridine (0.60mL, 6mmol), K2CO3 (1.38g) to 100mL Schlenk reaction flask under nitrogen atmosphere. ,10mmol). Ni(PPh3)Cl2 (159.3mg, 0.25mmol), DMF (5mL), and stirred at 90C for 24h. After the reaction, the mixture was diluted with water and extracted three times with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, the mixture was chromatographed on a silica gel column, eluted with petroleum ether/ethyl acetate=2:1, and drained to obtain a white solid (0.93g, 2.65mmol). The rate is 53%.
  • 24
  • [ 5315-25-3 ]
  • [ 637-87-6 ]
  • [ 61704-26-5 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 5315-25-3 ]

Bromides

Chemical Structure| 83004-10-8

A124523 [83004-10-8]

2-Bromo-6-(bromomethyl)pyridine

Similarity: 0.93

Chemical Structure| 79055-59-7

A126007 [79055-59-7]

2-Bromo-6-methylpyridin-4-amine

Similarity: 0.87

Chemical Structure| 4926-26-5

A236007 [4926-26-5]

2-Bromo-4,6-dimethylpyridine

Similarity: 0.87

Chemical Structure| 83004-13-1

A323538 [83004-13-1]

2-Bromo-6-ethylpyridine

Similarity: 0.87

Chemical Structure| 126325-53-9

A494266 [126325-53-9]

2-Bromo-6-methylpyridin-3-amine

Similarity: 0.87

Related Parent Nucleus of
[ 5315-25-3 ]

Pyridines

Chemical Structure| 83004-10-8

A124523 [83004-10-8]

2-Bromo-6-(bromomethyl)pyridine

Similarity: 0.93

Chemical Structure| 79055-59-7

A126007 [79055-59-7]

2-Bromo-6-methylpyridin-4-amine

Similarity: 0.87

Chemical Structure| 4926-26-5

A236007 [4926-26-5]

2-Bromo-4,6-dimethylpyridine

Similarity: 0.87

Chemical Structure| 83004-13-1

A323538 [83004-13-1]

2-Bromo-6-ethylpyridine

Similarity: 0.87

Chemical Structure| 126325-53-9

A494266 [126325-53-9]

2-Bromo-6-methylpyridin-3-amine

Similarity: 0.87