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Chemical Structure| 380380-64-3 Chemical Structure| 380380-64-3
Chemical Structure| 380380-64-3

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Product Details of 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine

CAS No. :380380-64-3
Formula : C7H6BrN5
M.W : 240.06
SMILES Code : CN1N=C(C2=NC=C(Br)C=C2)N=N1
MDL No. :MFCD06796604
InChI Key :JANKGNBDRWYWSN-UHFFFAOYSA-N
Pubchem ID :23438653

Safety of 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H315-H319-H228
Precautionary Statements:P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313
Class:4.1
UN#:1325
Packing Group:

Application In Synthesis of 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine

* 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 [ 380380-64-3 ]
  • Downstream synthetic route of [ 380380-64-3 ]

[ 380380-64-3 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 380380-64-3 ]
  • [ 856866-72-3 ]
YieldReaction ConditionsOperation in experiment
48% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium chloride In N,N-dimethyl-formamide at 90℃; for 4 h; In a 100 ml reaction flask,Compound 7 (5.0 g, 10 mmol) and 50 ml of DMF were added,2- (1-methyl-tetrazol-5-yl) -5-bromopyridine (2.65, 11 mmol)Lithium chloride (1.7 g),1,1'-bis (diphenylphosphino) ferrocene] palladium chloride (1.0 g),The mixture was stirred at 90 ° C for 4 hours,After completion of the reaction,To room temperature,And extracted three times with water / ethyl acetate (V / V = 1: 1)The organic layers were combined,Dried over anhydrous sodium sulfate,And concentrated to give 1.7 g of the compound (1)The yield was 48percent
26% With lithium chloride In 1-methyl-pyrrolidin-2-one at 20 - 120℃; for 4 h; In 150ml of 1-methyl-2-pyrrolidone was dissolved 37g of (R)-3- (4- tributhylstannyl-3-fluorophenyl)-2-oxo-5-oxazolidinylmethanol. The solution was added with 19.7g of 2- (2-methyltetrazol-5-yl)-5-bromopyridine, 10.44g of lithium chloride and 2.9g of dichlorobistriphenylphospine palladium (I I) at room temperature and then stirred at the temperature of 120 C for 4 hours. The reaction mixture was added with water and then extracted with ethyl acetate. The organic layer, thus separated, was washed with brine, dehydrated, filtrated, concentrated in vacuo and purified by column chromatography to provide 8g of the title compound. Yield 26percent. 1H NMR (DMSO-d6) 5 8.90 (s, lH), 8. 18 (m, 2H), 7.70 (m, 2H), 7.49 (dd, 1H), 5.25 (t, 1H), 4.74 (m, 1H), 4.46 (s, 3H), 4.14 (t, lH), 3. 88 (dd, lH), 3.68 (m, lH), 3. 58 (m, lH)
26% With bis-triphenylphosphine-palladium(II) chloride; lithium chloride In 1-methyl-pyrrolidin-2-one at 120℃; for 4 h; Inert atmosphere To a solution of (R)-3-(4-tributhylstannyl-3-fluorophenyl)-2-oxo-5-oxazolidinylmethanol 5 (37.0 g, 74.0 mmol) in NMP (150 mL) was added 2-(2-methyltetrazol-5-yl)-5-bromopyridine 9 (19.7 g, 81.9 mmol), LiCl (10.4 g, 245 mmol) and Pd(PPh3)2Cl2 (2.90 g, 4.13 mmol). The reaction mixture was stirred for 4 h at 120 °C. After being cooled to room temperature, the reaction mixture was poured into water and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was further purified by column chromatography to obtain the title compound (8 g, 26percent). Mp: 201 °C. 1H NMR (DMSO-d6): δ 8.90 (s, 1H), 8.18 (m, 2H), 7.70 (m, 2H), 7.49 (dd, J = 8.8 Hz, 2.4 Hz, 1H), 5.25 (t, J = 5.6 Hz, 1H), 4.74 (m, 1H), 4.46 (s, 3H), 4.14 (t, J = 8.8 Hz, 1H), 3.88 (m, 1H), 3.68 (m, 1H), 3.58 (m, 1H). 13C NMR (DMSO-d6): δ 163.56, 159.03, 154.06, 149.18, 144.78, 140.30, 136.96, 131.42, 130.73, 121.89, 118.36, 113.81, 105.18, 73.39, 61.52, 45.96, 39.63. IR (neat, cm-1): 3251.40, 1746.23, 1619.91, 1473.35, 1406.82. [M + H]+: 371.02. HRMS [EI-MS]: m/z, calculated for [C17H15FN6O3] 370.1190, found, 370.1100 [C17H15FN6O3].
References: [1] Patent: CN105859780, 2016, A, . Location in patent: Paragraph 0038.
[2] Patent: WO2005/58886, 2005, A1, . Location in patent: Page/Page column 28; 29.
[3] European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1027 - 1039.
[4] Patent: CN107400126, 2017, A, . Location in patent: Paragraph 0036.
  • 2
  • [ 444335-16-4 ]
  • [ 380380-64-3 ]
  • [ 856866-72-3 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; bis(pinacol)diborane In dimethyl sulfoxide at 80℃; for 14 h; Inert atmosphere
Stage #2: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 70℃; for 3 h; Inert atmosphere
DMSO (100 ml) was added to a 250 ml reaction flask,(5R) -3- (4-bromo-3-fluorophenyl) -5-hydroxymethyloxazolidin-2-one(10 g, 34.5 mmol), pinacolate (17.52 g, 69 mmol),[1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium dichloromethane complex (1.41 g, 1.73 mmol)And potassium acetate (13.5 g, 138 mmol), and the temperature was raised to 80 ° C under a nitrogen atmosphere,For 14 hours. The heating was stopped, the solution was cooled to room temperature, and extracted with water / ethyl acetate 3 times. The organic layers were combined and the organic layer was washed with saturated waterBrine, dried over anhydrous sodium sulfate and concentrated by suction filtration. The concentrated product of the above step was added to a 250 ml reaction flask,1,4-dioxane (100 ml) was added,5-bromo-2- (2-methyl-2H-tetrazol-5-yl) pyridine(8.28 g, 34.5 mmol),[1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium dichloromethane complex (0.56 g, 0.69 mmol)And cesium carbonate aqueous solution (50 ml, containing 33.72 g of cesium carbonate, 103.5 mmol),Under nitrogen protection,The temperature was raised to 70 ° C,The reaction was carried out for 3 hours,Dichloromethane was added for extraction.The separated organic phase was washed with saturated brine,Anhydrous sodium sulfate dehydration,filter,Concentrated in vacuo and purified by column chromatography,10.6 g of a solid was obtained,The yield was 83.0percentHPLC purity was 98.34percent (area normalization method).
References: [1] Patent: CN105418678, 2016, A, . Location in patent: Paragraph 0070; 0071; 0072; 0073; 0074; 0075.
  • 3
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References: [1] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 143 - 146.
 

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