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Chemical Structure| 124045-51-8 Chemical Structure| 124045-51-8

Structure of 124045-51-8

Chemical Structure| 124045-51-8

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Product Details of [ 124045-51-8 ]

CAS No. :124045-51-8
Formula : C9H15NO2
M.W : 169.22
SMILES Code : O=C(OC(C)(C)C)N(CC#C)C
MDL No. :MFCD22548360
InChI Key :QVMLIHFGUIRVKU-UHFFFAOYSA-N
Pubchem ID :18366137

Safety of [ 124045-51-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335-H227
Precautionary Statements:P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501

Application In Synthesis of [ 124045-51-8 ]

* 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 [ 124045-51-8 ]

[ 124045-51-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1050501-88-6 ]
  • [ 124045-51-8 ]
  • tert-butyl _ (3-(3-amino-6-chloropyridin-2-yl)prop-2-yn-1-yl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 70℃; for 17h;Inert atmosphere; Sealed tube; A mixture of tert-butyl methyl(prop-2-yl-1-yl)carbamate (612 mg, 3.62 mmol, Intermediate 11), <strong>[1050501-88-6]2-bromo-6-chloropyridin-3-amine</strong> (500 mg, 2.410 mmol, Fluorochem), copper I iodide (51 mg, 0.268 mmol, Sigma), PdCI2(dppf) (148 mg, 0.202 mmol, Manchester Organics) and TEA (0.504 ml_, 3.62 mmol, Sigma) in a sealed vial was degassed (purged and filled with nitrogen x 3) before adding anhydrous Tetrahydrofuran (THF) (10 ml_). The suspension was degassed by bubbling nitrogen through for 2 min. The reaction mixture was heated to 70 C for 17 hr. The reaction mixture was filtered through a 2.5g Celite SPE, eluting with ethyl actetate (30 ml.) and water (10 ml_). The reaction mixture was diluted with water (20 ml_), the aqueous extracted with ethyl acetate (3 x 30 ml_), combined organics washed with brine (20 ml_), dried through a hydrophobic frit and concentrated in vacuo and under nitrogen to give tert-butyl (3-(3-amino-6-chloropyridin-2-yl)prop-2-yn-1- yl)(methyl)carbamate (1.074 g, 2.360 mmol, 98 % yield) as a brown oil. 1H NMR (400 MHz, CHLOROFORM-d) d ppm 1.45 - 1.56 (m, 12 H) 3.00 (s, 3 H) 4.34 (s, 2 H) 6.96 - 7.13 (m, 2 H). LCMS (System B, UV, ESI) Rt = 1.08 min, [M+H]+ 240, 242
  • 2
  • [ 1050501-88-6 ]
  • [ 124045-51-8 ]
  • tert-butyl ((5-chloro-1H-pyrrolo[3,2-b]pyridin-2-yl)methyl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
9.339 g With pyrrolidine; bis-triphenylphosphine-palladium(II) chloride; In water; ethyl acetate; at 60℃; for 7h; A mixture of <strong>[1050501-88-6]2-bromo-6-chloropyridin-3-amine</strong> (11.15g, 53.7 mmol, Fluorochem), Intermediate 44 tert-butyl methyl(prop-2-yn-1-yl)carbamate (13.64 g, 81 mmol), pyrrolidine (22.22 ml, 269 mmol) and bis(triphenylphosphine)palladium(II) chloride (1.886 g, 2.69 mmol) was stirred and heated at 60C for 7 hours, LCMS showed mainly cyclised product. The reaction mixture was separated between ethyl acetate (250ml) and water (100ml). The organic phase was washed with brine (100ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The residue was dissolved in DCM and applied to a 330g silica cartridge. This was eluted with a gradient of 0- 100% ethyl acetate in cyclohexane over 30 minutes. The required fractions were combined and evaporated in vacuo to give tert-butyl ((5-chloro-1H-pyrrolo[3,2-b]pyridin-2-yl)methyl)(methyl)- carbamatetert-butyl methyl(prop-2-yn-1-yl)carbamate (9.339g) as a tan solid. LCMS (System B, UV, ESI): Rt = 1.03 min, [M+H]+ 296
 

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