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Chemistry
Heterocyclic Building Blocks
Pyridines
3-Bromo-5-(chloromethyl)pyridine
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Pyridines
Bromides Chlorides

[ CAS No. 120277-69-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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3d Animation Molecule Structure of 120277-69-2
Chemical Structure| 120277-69-2
Chemical Structure| 120277-69-2
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Quality Control of [ 120277-69-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 120277-69-2 ]

SDS Specification
Alternatived Products of [ 120277-69-2 ]

Product Details of [ 120277-69-2 ]

CAS No. :120277-69-2 MDL No. :MFCD10697600
Formula : C6H5BrClN Boiling Point : -
Linear Structure Formula :- InChI Key :NLPHAZLCNNDGPS-UHFFFAOYSA-N
M.W : 206.47 Pubchem ID :11701259
Synonyms :

Calculated chemistry of [ 120277-69-2 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.7
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) : -6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 1.93
Log Po/w (WLOGP) : 2.43
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 3.01
Consensus Log Po/w : 2.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.76
Solubility : 0.356 mg/ml ; 0.00172 mol/l
Class : Soluble
Log S (Ali) : -1.82
Solubility : 3.09 mg/ml ; 0.015 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.9
Solubility : 0.0258 mg/ml ; 0.000125 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.5

Safety of [ 120277-69-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 UN#:3261
Hazard Statements:H302-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 120277-69-2 ]

* 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 [ 120277-69-2 ]

[ 120277-69-2 ] Synthesis Path-Downstream   1~65

  • 1
  • [ 120277-69-2 ]
  • [ 120276-48-4 ]
Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1028 - 1036
  • 2
  • [ 120277-69-2 ]
  • [ 76944-95-1 ]
  • [ 258870-72-3 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2357 - 2363
  • 3
  • [ 120277-69-2 ]
  • (S)-3-Amino-1-(5-bromo-pyridin-3-ylmethyl)-azepan-2-one [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2357 - 2363
  • 4
  • [ 120277-69-2 ]
  • [ 258870-64-3 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2357 - 2363
  • 5
  • [ 120277-69-2 ]
  • (2S,3R)-3-{(S)-1-[5-(4-Methoxy-phenyl)-pyridin-3-ylmethyl]-2-oxo-azepan-3-ylcarbamoyl}-5-methyl-2-propyl-hexanoic acid [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2357 - 2363
  • 6
  • [ 120277-69-2 ]
  • (2R,3S)-2-Isobutyl-N1-{(S)-1-[5-(4-methoxy-phenyl)-pyridin-3-ylmethyl]-2-oxo-azepan-3-yl}-3-propyl-succinamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2357 - 2363
  • 7
  • [ 120277-69-2 ]
  • (2R,3S)-N1-{(S)-1-[5-(3-Chloro-4-fluoro-phenyl)-pyridin-3-ylmethyl]-2-oxo-azepan-3-yl}-2-isobutyl-3-propyl-succinamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2357 - 2363
  • 8
  • [ 120277-69-2 ]
  • (2S,3R)-3-{(S)-1-[5-(3-Chloro-4-fluoro-phenyl)-pyridin-3-ylmethyl]-2-oxo-azepan-3-ylcarbamoyl}-5-methyl-2-propyl-hexanoic acid [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2357 - 2363
  • 9
  • [ 120277-69-2 ]
  • [ 258870-49-4 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2357 - 2363
  • 10
  • [ 120277-69-2 ]
  • (2S,3R)-5-Methyl-3-{(S)-2-oxo-1-[5-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl]-azepan-3-ylcarbamoyl}-2-propyl-hexanoic acid [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2357 - 2363
  • 11
  • [ 120277-69-2 ]
  • [ 258870-50-7 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2357 - 2363
  • 12
  • [ 120277-69-2 ]
  • (2R,3S) N1-[(3S)-Hexahydro-1-(3-(4-trifluoromethylphenyl)pyrid-5-ylmethyl)-2-oxo-1H-azepin-3-yl]-2-(2-methylpropyl)-3-(propyl)-butanediamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2357 - 2363
  • 13
  • [ 120277-69-2 ]
  • (2S,3R)-5-Methyl-3-{(S)-2-oxo-1-[5-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl]-azepan-3-ylcarbamoyl}-2-propyl-hexanoic acid tert-butyl ester [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2357 - 2363
  • 14
  • [ 120277-69-2 ]
  • [ 120274-44-4 ]
Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1028 - 1036
  • 15
  • [ 120277-69-2 ]
  • [ 120276-40-6 ]
Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1028 - 1036
  • 16
  • [ 1603-91-4 ]
  • [ 120277-69-2 ]
  • 3-(5-bromo-3-pyridyl)methyl-2-imino-4-methyl-2,3-dihydrothiazole hydrochloride [ No CAS ]
Reference： [1]Patent: EP1176141,2002,A1 .Location in patent: Page 9-10
  • 17
  • [ 37669-64-0 ]
  • [ 120277-69-2 ]
YieldReaction ConditionsOperation in experiment
93% With thionyl chloride; In dichloromethane; at 0 - 20℃; To a solution of (5-bromopyridin-3-yl)methanol (3 g, 16.0 mmol) in DCM (15 mL) cooled to 0 C. was added thionylchloride (7.59 g, 63.8 mmol) dropwise and the reaction mixture was stirred at room temperature over night. The mixture was poured onto ice/water (20 mL), basified with NaOH conc. (8 mL) and extracted with EtOAc (2×50 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40% EtOAc-Heptane gradient to give the title compound (3.08 g, 93%) as a white solid. MS: 206.0, 207.9 (M+H+)
93% With thionyl chloride; In dichloromethane; at 20℃; Intermediate A-12 l-(5-Bromo-pyridin-3-ylmethyl)-pyrrolidin-2-one [A] 3 -Bromo-5 -chloromethyl-pyridineTo a solution of (5-bromopyridin-3-yl)methanol (3 g, 16.0 mmol) in DCM (15 mL) cooled to 0 C was added thionylchloride (7.59 g, 63.8 mmol) dropwise and the reaction mixture was stirred at room temperature over night. The mixture was poured onto ice/water (20 mL), basified with NaOH cone. (8 mL) and extracted with EtOAc (2 x 50 mL). Combined organics were dried over Na2S04, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40% EtO Ac-Heptane gradient to give the title compound (3.08 g, 93 %) as a white solid. MS: 206.0, 207.9 (M+H+).
93% With thionyl chloride; In dichloromethane; at 0 - 20℃;Inert atmosphere; To a solution of (5-bromopyridin-3-yl)methanol (3 g, 16.0 mmol) in DCM (15 mL) cooled to 0 C was added thionylchloride (7.59 g, 63.8 mmol) dropwise and the reaction mixture was stirred at room temperature over night. The mixture was poured onto ice/water (20 mL), basified with NaOH cone. (8 mL) and extracted with EtOAc (2 x 50 mL). Combined organics were dried over Na2S04, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40% EtO Ac-heptane gradient to give the title compound (3.08 g, 93 %) as a white solid. MS: 206.0, 207.9 (M+H+).
93% With thionyl chloride; In dichloromethane; at 20℃; [B] 3-Bromo-5-chloromethyl-pyridine At 0 C., to a solution of (5-bromopyridin-3-yl)methanol (3 g, 16.0 mmol) in DCM (15 mL) was added thionylchloride (7.59 g, 63.8 mmol) dropwise and the reaction mixture was stirred at room temperature overnight. The mixture was poured onto ice/water (20 mL), and basified with conc. NaOH solution (8 mL). The mixture was extracted with EtOAc (2*50 mL) and combined organic layers were dried over anhy. Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40% EtOAc-heptane gradient to give the title compound (3.08 g, 93%) as a white solid. MS: 206.0, 207.9 (M+H+).
93% With thionyl chloride; In dichloromethane; at 20℃; To a solution of (5-bromopyridin-3-yl)methanol (1 g, 5.32 mmol) in DCM (5 mL) was added thionyl chloride (2.53 g, 21.3 mmol) dropwise and the reaction mixture was stirred at room temperature over night. The mixture was diluted with DCM, poured into a 20 % aq. NaOH solution (20 mL) and the resulting solution was extracted with DCM (2 x 25 mL). Combined organics were washed with brine, dried over Na2S04, filtered and evaporated to dryness to give to the title compound (1.02 g, 93 %) as a light brown solid. MS: 208.3 (M+H+).
84% With thionyl chloride; 3-Bromo-5-(chloromethyl)-pyridine To a cooled solution of thionylchloride (41 ml, 344 mmol) at 0 C. was added cautiously (highly exothermic) portionwise (5-bromo-pyridin-3-yl)-methanol (10 g, 44.5 mmol). After complete addition the mixture was heated to reflux for 1 h to complete the reaction. After cooling, ether (50 ml) was added and the mixture cooled to 4 C. The precipitated solid was filtered off and washed with cold ether then dried at 50 C. under vacuum for 2 h to afford the title compound (9.1 g, 84%) as a light yellow solid. MS: m/e=206.9 (M+).
82% With thionyl chloride; In dichloromethane; at 20℃; for 2h;Product distribution / selectivity; To a solution of (5-bromo-pyridin-3-yl)-methanol, (0.500 g, 2.68 mmol) DCM (10 mL) was added thionyl chloride (0.5 mL) and the resulting solution was stirred at room temperature for 2 h. The reaction mixture was quenched by the addition of water and extracted into DCM. The organic extracts were washed with brine filtered and concentrated under reduced pressure to provide 3-bromo-5- chloromethyl-pyridine (0.45 g, 82 %), which was used without further purification.

Reference： [1]Patent: US2013/72679,2013,A1 .Location in patent: Paragraph 0586; 0587
[2]Patent: WO2013/37779,2013,A1 .Location in patent: Page/Page column 84; 85
[3]Patent: WO2013/79452,2013,A1 .Location in patent: Page/Page column 173
[4]Patent: US2013/143863,2013,A1 .Location in patent: Paragraph 1244
[5]Patent: WO2014/139981,2014,A1 .Location in patent: Page/Page column 25
[6]Patent: US2002/151715,2002,A1
[7]Patent: WO2011/28741,2011,A1 .Location in patent: Page/Page column 287
[8]Journal of Medicinal Chemistry,2012,vol. 55,p. 3201 - 3215
[9]Journal of Medicinal Chemistry,2015,vol. 58,p. 1067 - 1088
  • 18
  • potassium cyanide [ No CAS ]
  • [ 120277-69-2 ]
  • [ 39891-08-2 ]
YieldReaction ConditionsOperation in experiment
46.5% In N,N-dimethyl-formamide; at 20℃; for 16h;Product distribution / selectivity; 3-Bromo-5-chloromethyl-pyridine (0.45 g; 2.2 mmol) was dissolved in DMF (10 mL). Potassium cyanide (0.21 g, 3.27 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was quenched by the addition of water and extracted with ethyl acetate. The organic phases were washed with water, brine and dried over a2S03 filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 7 % EtOAc in Hexanes to provide 2-(5-bromopyridin-3-yl) acetonitrile (200 mg, 46.5 %). XH NMR (400 MHz, DMSO-i¾) delta (ppm): 8.68 (d, 1H, J= 2Hz), 8.51 (d, 1H, J= 2Hz), 7.88 (t, 1H, J= 2Hz), 3.77 (s, 2H).
Reference： [1]Patent: WO2011/28741,2011,A1 .Location in patent: Page/Page column 287
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 1067 - 1088
  • 19
  • [ 120277-69-2 ]
  • [ 1272356-97-4 ]
Reference： [1]Patent: WO2011/28741,2011,A1
  • 20
  • [ 120277-69-2 ]
  • [ 1272355-08-4 ]
Reference： [1]Patent: WO2011/28741,2011,A1
  • 21
  • [ 120277-69-2 ]
  • [ 1272355-11-9 ]
Reference： [1]Patent: WO2011/28741,2011,A1
  • 22
  • [ 120277-69-2 ]
  • [ 1272357-11-5 ]
Reference： [1]Patent: WO2011/28741,2011,A1
  • 23
  • [ 120277-69-2 ]
  • [ 1272357-12-6 ]
Reference： [1]Patent: WO2011/28741,2011,A1
  • 24
  • [ 120277-69-2 ]
  • [ 1272357-13-7 ]
Reference： [1]Patent: WO2011/28741,2011,A1
  • 25
  • [ 120277-69-2 ]
  • [ 1272357-14-8 ]
Reference： [1]Patent: WO2011/28741,2011,A1
  • 26
  • [ 120277-69-2 ]
  • [ 1272355-30-2 ]
Reference： [1]Patent: WO2011/28741,2011,A1
  • 27
  • [ 120277-69-2 ]
  • [ 1272357-15-9 ]
  • [ 1272357-16-0 ]
Reference： [1]Patent: WO2011/28741,2011,A1
  • 28
  • [ 120277-69-2 ]
  • [ 1272357-22-8 ]
Reference： [1]Patent: WO2011/28741,2011,A1
  • 29
  • [ 120277-69-2 ]
  • [ 1272357-23-9 ]
Reference： [1]Patent: WO2011/28741,2011,A1
  • 30
  • [ 120277-69-2 ]
  • [ 1272355-37-9 ]
Reference： [1]Patent: WO2011/28741,2011,A1
  • 31
  • [ 20826-04-4 ]
  • [ 120277-69-2 ]
Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3201 - 3215
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 1067 - 1088
  • 32
  • [ 120277-69-2 ]
  • [ 1365537-85-4 ]
Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3201 - 3215
  • 33
  • [ 120277-69-2 ]
  • [ 1660-94-2 ]
  • [ 1365537-84-3 ]
Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3201 - 3215
  • 34
  • [ 616-45-5 ]
  • [ 120277-69-2 ]
  • [ 173999-28-5 ]
YieldReaction ConditionsOperation in experiment
87% To a suspension of sodium hydride (60% in mineral oil, 0.044 g, 1.09 mmol) in DMF (2 mL) was added pyrrolidin-2-one (0.081 g, 0.945 mmol) and the reaction mixture was stirred at room temperature for 20 min. Then, <strong>[120277-69-2]3-bromo-5-chloromethyl-pyridine</strong> (0.15 g, 0.727 mmol) was added and the resulting suspension was heated at 60 C. over night. The mixture was quenched with water (2 mL) and extracted with EtOAc (2×10 mL). Combined organics were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.217 g, 87%) as a white solid. MS: 251.1, 257.1 (M+H+)
87% [B] 1 -(5-Bromo-pyridin-3-ylmethyl)-pyrrolidin-2-oneTo a suspension of sodium hydride (60% in mineral oil, 0.044 g, 1.09 mmol) in DMF (2 mL) was added pyrrolidin-2-one (0.081 g, 0.945 mmol) and the reaction mixture was stirred at room temperature for 20 min. Then, <strong>[120277-69-2]3-bromo-5-chloromethyl-pyridine</strong> (0.15 g,0.727 mmol) was added and the resulting suspension was heated at 60 C over night. The mixture was quenched with water (2 mL) and extracted with EtO Ac (2 x 10 mL).Combined organics were dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.217 g, 87 %) as a white solid. MS: 251.1,257.1 (M+H+).
Reference： [1]Patent: US2013/72679,2013,A1 .Location in patent: Paragraph 0588; 0589
[2]Patent: WO2013/37779,2013,A1 .Location in patent: Page/Page column 85
  • 35
  • [ 120277-69-2 ]
  • [ 79-05-0 ]
  • [ 1427588-53-1 ]
YieldReaction ConditionsOperation in experiment
82% To a solution of propionamide (146 mg, 2.0 mmol) in DMF (10 mL) was added NaH (61 mg, 2.4 mmol) at 0 C. and reaction mixture was stirred for 10 min before the addition of <strong>[120277-69-2]3-bromo-5-chloromethyl-pyridine</strong> (intermediate A-12 [A], 412 mg, 2.0 mmol). The resulting reaction mixture was stirred at room temperature for 1 hour before water was added. Then, the reaction mixture was extracted with EtOAc and combined organic layers were dried by anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was then purified by flash chromatography to give title compound (400 mg, 82%) as a solid.
82% Example 212 N-[5-(7-Fluoro-l-methyl-2-oxo-l,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]- propionamide [A] N-(5-Bromo-pyridin-3-ylmethyl)-propionamideTo a solution of propionamide (146 mg, 2.0 mmol) in DMF (10 mL) was added NaH (61 mg, 2.4 mmol) at 0 C and reaction mixture was stirred for 10 min before the addition of 3- bromo-5-chloromethyl-pyridine (intermediate A-12 [A], 412 mg, 2.0 mmol). The resulting reaction mixture was stirred at room temperature for 1 hour before water was added. Then, the reaction mixture was extracted with EtOAc and combined organic layers were dried by anhydrous Na2S04, filtered and concentrated in vacuo. The residue was then purified by flash chromatography to give title compound (400 mg, 82%) as a solid.
Reference： [1]Patent: US2013/72679,2013,A1 .Location in patent: Paragraph 0886; 0887
[2]Patent: WO2013/37779,2013,A1 .Location in patent: Page/Page column 233; 234
  • 36
  • [ 120277-69-2 ]
  • [ 1427586-77-3 ]
Reference： [1]Patent: WO2013/37779,2013,A1
[2]Patent: US2013/72679,2013,A1
  • 37
  • [ 113118-81-3 ]
  • [ 120277-69-2 ]
Reference： [1]Patent: WO2013/79452,2013,A1
[2]Patent: US2013/143863,2013,A1
  • 38
  • [ 120277-69-2 ]
  • [ 135124-70-8 ]
YieldReaction ConditionsOperation in experiment
27% With ammonia; In methanol; at 60℃; [C] (5-Bromo-pyridin-3-yl)-methylamine 3-Bromo-5-chloromethyl-pyridine (10.3 g, 50 mmol) was dissolved in ammonia methanol solution (7 N, 250 ml) and heated at 60 C. overnight. After aq. NaOH (1N) solution was added to adjust the pH to >12, the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo. The crude product was purified by recrystallization to give title compound as a solid (2.5 g, 27%). MS: 187.1 (M+H+).
Reference： [1]Patent: US2013/143863,2013,A1 .Location in patent: Paragraph 1245; 1246
  • 39
  • [ 120277-69-2 ]
  • [ 1440520-24-0 ]
Reference： [1]Patent: US2013/143863,2013,A1
  • 40
  • [ 120277-69-2 ]
  • [ 1440519-04-9 ]
Reference： [1]Patent: US2013/143863,2013,A1
  • 41
  • [ 36947-68-9 ]
  • [ 120277-69-2 ]
  • [ 1440520-53-5 ]
YieldReaction ConditionsOperation in experiment
81% To a suspension of sodium hydride (60% in mineral oil, 0.073 g, 1.82 mmol) in DMF (3 mL) was added 2-isopropyl-lH- imidazole (0.173 g, 1.57 mmol) and the reaction mixture was stirred at room temperature for 20 min. Then, <strong>[120277-69-2]3-bromo-5-chloromethyl-pyridine</strong> (0.25 g, 1.21 mmol) was added and the resulting suspension was heated at 60 C over night. The mixture was quenched with water (2 mL) and extracted with EtO Ac (2x 10 mL).Combined organics were dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH- - 174 -DCM gradient to give the title compound (0.275 g, 81 %) as a light yellow oil. MS: 280.0, 282.0 (M+H+).
Reference： [1]Patent: WO2013/79452,2013,A1 .Location in patent: Page/Page column 173; 174
  • 42
  • [ 120277-69-2 ]
  • 9-nitro-3,4,5,6-tetrahydro-2H-imidazo[2,1-b][1,3,6]oxadiazocine hydrochloride [ No CAS ]
  • [ 1437110-80-9 ]
YieldReaction ConditionsOperation in experiment
36% 4-((5-Bromopyridin-3-yl)methyl)-9-nitro-3,4,5,6-tetrahydro-2H- imidazo[2,1-b][1 ,3,6]oxadiazocine (7.2.13)A solution of <strong>[120277-69-2]3-bromo-5-(chloromethyl)pyridine</strong>(0.042 g, 0.202 mmol) in acetone (5 mL) was treated with sodium iodide (0.151 g, 1 .01 mmol). The mixture was refluxed for an hour. Potassium carbonate (0.167 g, 1 .21 mmol) was added to the reaction.9-nitro-3,4,5,6-tetrahydro-2H-imidazo[2, 1 - b][1 ,3,6]oxadiazocine 7.1.3 (0.04 g, 0.202 mmol) was dissolved in acetone and added to the stirring mixture. The reaction mixture was filtered, evaporated and submitted through preparative HPLC to obtain 4-((5- bromopyridin-3-yl)methyl)-9-nitro-3,4,5,6-tetrahydro-2H-imidazo[2,1 -b] [1 ,3,6] oxadiazocine (26.9 g, 0.073 mmol, 36%). See Table 19 for analytical data.
Reference： [1]Patent: WO2013/72903,2013,A1 .Location in patent: Page/Page column 98
  • 43
  • [ 16879-02-0 ]
  • [ 120277-69-2 ]
  • 2-((5-bromopyridin-3-yl)methoxy)-6-chloropyridine [ No CAS ]
  • 1-(5-bromo-pyridin-3-ylmethyl)-6-chloro-1H-pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
69%; 15% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 6h; To a solution of <strong>[120277-69-2]3-bromo-5-chloromethyl-pyridine</strong> (0.05 g, 0.242 mmol) in DMF (1 mL) were added 6-chloro-lH-pyridin-2-one (0.031 g, 0.242 mmol) and K2C03 (0.067 g, 0.484 mmol) and the reaction mixture was stirred at room temperature for 6 h. The mixture was diluted with EtOAc, poured into H20 (3 mL) and the aqueous layer was extracted with EtOAc (2 x 10 mL). Combined organics were dried over Na2S04, filtered and evaporated. The residue was purified by silica gel flash chromatography eluting with a 0 to 100% EtO Ac-heptane gradient to give 2- ((5-bromopyridin-3-yl)methoxy)-6-chloropyridine (0.05 g, 69 %) as a colorless liquid, MS: 301.3 (M+H+); and l-(5-bromo-pyridin-3-ylmethyl)-6-chloro-lH-pyridin-2-one (0.011 g, 15 %) as a yellow solid. MS: 301.3 (M+H+).
Reference： [1]Patent: WO2014/139981,2014,A1 .Location in patent: Page/Page column 25; 26
  • 44
  • [ 934-34-9 ]
  • [ 120277-69-2 ]
  • 3-(5-bromopyridin-3-ylmethyl)-3H-benzothiazol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 6h; General procedure: To a solution of <strong>[120277-69-2]3-bromo-5-chloromethyl-pyridine</strong> (0.05 g, 0.242 mmol) in DMF (1 mL) were added 6-chloro-lH-pyridin-2-one (0.031 g, 0.242 mmol) and K2C03 (0.067 g, 0.484 mmol) and the reaction mixture was stirred at room temperature for 6 h. The mixture was diluted with EtOAc, poured into H20 (3 mL) and the aqueous layer was extracted with EtOAc (2 x 10 mL). Combined organics were dried over Na2S04, filtered and evaporated. The residue was purified by silica gel flash chromatography eluting with a 0 to 100% EtO Ac-heptane gradient to give 2- ((5-bromopyridin-3-yl)methoxy)-6-chloropyridine (0.05 g, 69 %) as a colorless liquid, MS: 301.3 (M+H+); and l-(5-bromo-pyridin-3-ylmethyl)-6-chloro-lH-pyridin-2-one (0.011 g, 15 %) as a yellow solid. MS: 301.3 (M+H+). The following intermediates listed in Table 1 were prepared from 3-bromo-5-chloromethyl- pyridine (intermediate A-2 [A]), in analogy to the procedure described for the preparation of intermediates A-2 [B], using appropriate reaction partners.
Reference： [1]Patent: WO2014/139981,2014,A1 .Location in patent: Page/Page column 25; 26; 28
  • 45
  • [ 6039-97-0 ]
  • [ 120277-69-2 ]
  • 3-(5-bromopyridin-3-ylmethyl)-3H-thiazol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 6h; General procedure: To a solution of <strong>[120277-69-2]3-bromo-5-chloromethyl-pyridine</strong> (0.05 g, 0.242 mmol) in DMF (1 mL) were added 6-chloro-lH-pyridin-2-one (0.031 g, 0.242 mmol) and K2C03 (0.067 g, 0.484 mmol) and the reaction mixture was stirred at room temperature for 6 h. The mixture was diluted with EtOAc, poured into H20 (3 mL) and the aqueous layer was extracted with EtOAc (2 x 10 mL). Combined organics were dried over Na2S04, filtered and evaporated. The residue was purified by silica gel flash chromatography eluting with a 0 to 100% EtO Ac-heptane gradient to give 2- ((5-bromopyridin-3-yl)methoxy)-6-chloropyridine (0.05 g, 69 %) as a colorless liquid, MS: 301.3 (M+H+); and l-(5-bromo-pyridin-3-ylmethyl)-6-chloro-lH-pyridin-2-one (0.011 g, 15 %) as a yellow solid. MS: 301.3 (M+H+). The following intermediates listed in Table 1 were prepared from 3-bromo-5-chloromethyl- pyridine (intermediate A-2 [A]), in analogy to the procedure described for the preparation of intermediates A-2 [B], using appropriate reaction partners.
Reference： [1]Patent: WO2014/139981,2014,A1 .Location in patent: Page/Page column 25; 26; 28
  • 46
  • [ 13466-35-8 ]
  • [ 120277-69-2 ]
  • 1-(5-bromopyridin-3-ylmethyl)-3-chloro-1-pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 6h; General procedure: To a solution of <strong>[120277-69-2]3-bromo-5-chloromethyl-pyridine</strong> (0.05 g, 0.242 mmol) in DMF (1 mL) were added 6-chloro-lH-pyridin-2-one (0.031 g, 0.242 mmol) and K2C03 (0.067 g, 0.484 mmol) and the reaction mixture was stirred at room temperature for 6 h. The mixture was diluted with EtOAc, poured into H20 (3 mL) and the aqueous layer was extracted with EtOAc (2 x 10 mL). Combined organics were dried over Na2S04, filtered and evaporated. The residue was purified by silica gel flash chromatography eluting with a 0 to 100% EtO Ac-heptane gradient to give 2- ((5-bromopyridin-3-yl)methoxy)-6-chloropyridine (0.05 g, 69 %) as a colorless liquid, MS: 301.3 (M+H+); and l-(5-bromo-pyridin-3-ylmethyl)-6-chloro-lH-pyridin-2-one (0.011 g, 15 %) as a yellow solid. MS: 301.3 (M+H+). The following intermediates listed in Table 1 were prepared from 3-bromo-5-chloromethyl- pyridine (intermediate A-2 [A]), in analogy to the procedure described for the preparation of intermediates A-2 [B], using appropriate reaction partners.
Reference： [1]Patent: WO2014/139981,2014,A1 .Location in patent: Page/Page column 25; 26; 29
  • 47
  • [ 120277-69-2 ]
  • 3-fluoro-5-trifluoromethyl-1H-pyridin-2-one [ No CAS ]
  • 1-(5-bromopyridin-3-ylmethyl)-3-fluoro-5-trifluoromethyl-1-pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 6h; General procedure: To a solution of <strong>[120277-69-2]3-bromo-5-chloromethyl-pyridine</strong> (0.05 g, 0.242 mmol) in DMF (1 mL) were added 6-chloro-lH-pyridin-2-one (0.031 g, 0.242 mmol) and K2C03 (0.067 g, 0.484 mmol) and the reaction mixture was stirred at room temperature for 6 h. The mixture was diluted with EtOAc, poured into H20 (3 mL) and the aqueous layer was extracted with EtOAc (2 x 10 mL). Combined organics were dried over Na2S04, filtered and evaporated. The residue was purified by silica gel flash chromatography eluting with a 0 to 100% EtO Ac-heptane gradient to give 2- ((5-bromopyridin-3-yl)methoxy)-6-chloropyridine (0.05 g, 69 %) as a colorless liquid, MS: 301.3 (M+H+); and l-(5-bromo-pyridin-3-ylmethyl)-6-chloro-lH-pyridin-2-one (0.011 g, 15 %) as a yellow solid. MS: 301.3 (M+H+). The following intermediates listed in Table 1 were prepared from 3-bromo-5-chloromethyl- pyridine (intermediate A-2 [A]), in analogy to the procedure described for the preparation of intermediates A-2 [B], using appropriate reaction partners.
Reference： [1]Patent: WO2014/139981,2014,A1 .Location in patent: Page/Page column 25; 26; 29
  • 48
  • [ 120277-69-2 ]
  • [ 1547-29-1 ]
  • 1-(5-bromopyridin-3-ylmethyl)-3-fluoro-1-pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 6h; General procedure: To a solution of <strong>[120277-69-2]3-bromo-5-chloromethyl-pyridine</strong> (0.05 g, 0.242 mmol) in DMF (1 mL) were added 6-chloro-lH-pyridin-2-one (0.031 g, 0.242 mmol) and K2C03 (0.067 g, 0.484 mmol) and the reaction mixture was stirred at room temperature for 6 h. The mixture was diluted with EtOAc, poured into H20 (3 mL) and the aqueous layer was extracted with EtOAc (2 x 10 mL). Combined organics were dried over Na2S04, filtered and evaporated. The residue was purified by silica gel flash chromatography eluting with a 0 to 100% EtO Ac-heptane gradient to give 2- ((5-bromopyridin-3-yl)methoxy)-6-chloropyridine (0.05 g, 69 %) as a colorless liquid, MS: 301.3 (M+H+); and l-(5-bromo-pyridin-3-ylmethyl)-6-chloro-lH-pyridin-2-one (0.011 g, 15 %) as a yellow solid. MS: 301.3 (M+H+). The following intermediates listed in Table 1 were prepared from 3-bromo-5-chloromethyl- pyridine (intermediate A-2 [A]), in analogy to the procedure described for the preparation of intermediates A-2 [B], using appropriate reaction partners.
Reference： [1]Patent: WO2014/139981,2014,A1 .Location in patent: Page/Page column 25; 26; 30
  • 49
  • [ 622-40-2 ]
  • [ 120277-69-2 ]
  • 6-[5-(2-morpholinoethoxymethyl)-3-pyridyl]-3,4-dihydro-2H-1,8-naphthyridine-1-carboxamide [ No CAS ]
Reference： [1]Patent: US2014/323468,2014,A1
  • 50
  • [ 120277-69-2 ]
  • [ 623-50-7 ]
  • (5-bromo-pyridin-3-ylmethoxy)-acetic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.6 g Hydroxy-acetic acid ethyl ester (3.7 g, 36 mmol) is added to a suspension of 60% NaH (1.5 g, 37 mmol) in DMF (70 ml) at 0 C. and the mixture is stirred at room temperature for 15 min. Then <strong>[120277-69-2]3-bromo-5-chloromethyl-pyridine</strong> (3.0 g, 15 mmol) is added to the mixture at 0 C. and the mixture is stirred at room temperature for 16 hrs. The reaction is quenched with saturated. NH4Cl aqueous solution, extracted with EtOAc three times. The organic layers are combined, washed with water and brine, dried over Na2SO4 and concentrated. The residue is purified by flash column chromatography to give 1.6 g of (5-bromo-pyridin-3-ylmethoxy)-acetic acid ethyl ester.
Reference： [1]Patent: US2014/323468,2014,A1 .Location in patent: Paragraph 0530
  • 51
  • [ 120277-69-2 ]
  • 1-(5-bromo-pyridin-3-ylmethoxy)-2-methyl-propan-2-ol [ No CAS ]
Reference： [1]Patent: US2014/323468,2014,A1
  • 52
  • [ 622-40-2 ]
  • [ 120277-69-2 ]
  • 4-[2-[(5-bromo-3-pyridyl)methoxy]ethyl]morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
370 mg To the NaH (484 mg, 60% in mineral oil, 12.1 mmol) in DMF (dry, 1 mL) at 0 C., is slowly added 2-morpholin-4-yl-ethanol (1.47 ml, 12.1 mmol). Then the mixture is stirred at 0 C. for 30 min. <strong>[120277-69-2]3-bromo-5-chloromethyl-pyridine</strong> (500 mg, 2.42 mmol) is added at 0 C. The mixture is then stirred at room temperature overnight and is quenched by adding water dropwise. The mixture is partitioned between DCM and water. The DCM phase is separated and then washed with water twice. The DCM phase is evaporated under high vacuum. The residue is separated by silica gel flash column (MeOH/ DCM 0 to 5% gradient, then 5%) to obtain 370 mg of 4-[2-[(5-bromo-3-pyridyl)methoxy]ethyl]morpholine.
Reference： [1]Patent: US2014/323468,2014,A1 .Location in patent: Paragraph 0562
  • 53
  • [ 120277-69-2 ]
  • 2-(5-bromopyridin-3-yl)acetaldehyde [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1067 - 1088
  • 54
  • [ 120277-69-2 ]
  • C15H14BrFN2 [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1067 - 1088
  • 55
  • [ 120277-69-2 ]
  • C20H24BrFN2O2 [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1067 - 1088
  • 56
  • [ 120277-69-2 ]
  • 2-[5-(1H-imidazol-1-yl)pyridin-3-yl]-N-(3-fluorophenethyl)ethan-1-amine trihydrochloride [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1067 - 1088
  • 57
  • [ 120277-69-2 ]
  • 2-(5-bromopyridin-3-yl)-N-(3-fluorophenethyl)ethan-1-amine [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1067 - 1088
  • 58
  • [ 120277-69-2 ]
  • tert-butyl 2-[5-(1H-imidazol-1-yl)pyridin-3-yl]ethyl-3-fluorophenethylcarbamate [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1067 - 1088
  • 59
  • [ 120277-69-2 ]
  • 5-chloro-4-((3-(2,3-dihydrobenzo[b][1,4]dioxine-6-yl)-2-methylbenzyl)oxy)-2-hydroxylbenzaldehyde [ No CAS ]
  • 2-((5-bromopyridin-3-yl)methoxy)-5-chloro-4-(3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methylbenzyloxy)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 75℃; for 3h; Cesium carbonate (159 mg, 0.487 mmol), 5-chloro-4-((3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methylbenzyl)oxy)-2-hydroxybenzaldehyde (100 mg, 0.243 mmol) and 5-(chloromethyl)nicotinonitrile (74.3 mg, 0.487 mmol) were stirred at 75 C. for 3 hours in dimethyl formamide (1 mL). (0655) The reaction was neutralized with dilute hydrochloric acid (0.1 N) and washed with water and brine. Dried over sodium sulfate. The residue was purified with 1:1 to 1:2 hexane:ethyl acetate on a 12 g silica gel column Collected fractions to afford a yellow solid as desired product. LCMS Condition T: 1.46 minutes, M+1=527.3.
Reference： [1]Patent: US2015/291549,2015,A1 .Location in patent: Paragraph 0653-0655
  • 60
  • [ 867267-28-5 ]
  • [ 120277-69-2 ]
  • 5-((5-bromopyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde [ No CAS ]
Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 321 - 326
  • 61
  • [ 120277-69-2 ]
  • tert-butyl (5S)-3-oxo-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate [ No CAS ]
  • tert-butyl (5S)-2-[(5-bromopyridin-3-yl)methyl]-3-oxo-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With caesium carbonate; In acetonitrile; tert-Butyl (5S)-2-[(5-bromopyridin-3-yl)methyl]-3-oxo-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate tert-Butyl (5S)-3-oxo-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate (396 mg, 1.66 mmol) was initially charged in acetonitrile (6.6 ml). Caesium carbonate (1.08 g, 3.31 mmol) and <strong>[120277-69-2]3-bromo-5-(chloromethyl)pyridine</strong> (376 mg, 1.82 mmol) were subsequently added. After stirring overnight, the reaction mixture was admixed at room temperature with water and ethyl acetate. The organic phase was removed and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and filtered, and the filtrate was concentrated. The residue was purified via preparative HPLC (Chromatorex C18, 10 mum, 125 mm*30 mm; eluent: acetonitrile/water gradient). The product-containing fractions were concentrated under reduced pressure, and 146 mg (22% of theory) of the title compound were obtained. LC-MS (Method 3): Rt=1.64 min; MS (ESIpos): m/z=409 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) delta[ppm]: 1.390 (16.00), 2.066 (0.53), 2.075 (0.53), 2.640 (0.40), 4.458 (0.61), 4.926 (1.27), 4.939 (1.25), 7.915 (0.87), 8.468 (0.83), 8.472 (0.90), 8.643 (0.71), 8.649 (0.75).
Reference： [1]Patent: US2019/160048,2019,A1 .Location in patent: Paragraph 1857-1860
  • 62
  • [ 120277-69-2 ]
  • [ 24424-99-5 ]
  • [ 943722-24-5 ]
Reference： [1]Journal of Medicinal Chemistry,2020
  • 63
  • [ 120277-69-2 ]
  • C16H16N4 [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2020
  • 64
  • [ 120277-69-2 ]
  • 7-(5-(aminomethyl)pyridin-3-yl)-4-methylquinolin-2-amine trihydrochloride [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2020
  • 65
  • [ 120277-69-2 ]
  • C21H24N4O2 [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2020

Tags: 120277-69-2 synthesis path| 120277-69-2 SDS| 120277-69-2 COA| 120277-69-2 purity| 120277-69-2 application| 120277-69-2 NMR| 120277-69-2 COA| 120277-69-2 structure

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