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[ CAS No. 5315-25-3 ] {[proInfo.proName]}

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Chemical Structure| 5315-25-3
Chemical Structure| 5315-25-3
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Product Details of [ 5315-25-3 ]

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

Calculated chemistry of [ 5315-25-3 ]      Expand+

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 ?2

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:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
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.

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

[ 5315-25-3 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 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)
  • 2
  • [ 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.
  • 3
  • [ 5315-25-3 ]
  • [ 62674-71-9 ]
  • 6
  • [ 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)
  • 7
  • [ 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)

  • 8
  • [ 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]+.
  • 9
  • [ 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)
  • 10
  • [ 5315-25-3 ]
  • [ 115-19-5 ]
  • [ 30413-58-2 ]
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