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Chemical Structure| 914347-21-0 Chemical Structure| 914347-21-0

Structure of 914347-21-0

Chemical Structure| 914347-21-0

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Product Details of [ 914347-21-0 ]

CAS No. :914347-21-0
Formula : C12H10BrNO2S
M.W : 312.18
SMILES Code : O=C(C1=C(Br)SC(C2=CC=CC=C2)=N1)OCC
MDL No. :MFCD08275710
InChI Key :ONAJVAODOMRERW-UHFFFAOYSA-N
Pubchem ID :44558337

Safety of [ 914347-21-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 914347-21-0 ]

* 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 [ 914347-21-0 ]

[ 914347-21-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 59937-01-8 ]
  • [ 914347-21-0 ]
  • 2
  • [ 914347-21-0 ]
  • [ 627-41-8 ]
  • [ 1231952-89-8 ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In 1,2-dimethoxyethane; for 16.0h;Inert atmosphere; Reflux; Nitrogen was bubbled through a solution of Ethyl 5-bromo-2-phenylthiazole-4-carboxylate (13.1 g, 41.9 mmol) and methyl propargyl ether (7.1 mL, 83.9 mmol) in dimethoxy ethane (DME) (200 mL). Dichlorobis(triphenylphosphine)palladium (II) (1.47 g, 2.2 mmol), copper (I) iodide (0.2 g, 1.1 mmol), and TEA (29 mL, 210 mmol) were added and the reaction mixture was heated at reflux for 16 h. The reaction mixture was cooled to room temperature, poured into H2O (200 mL) and extracted with EtOAc (2 X 200 mL). The combined organics were washed with brine, dried (MgSO4), and concentrated. The crude product was purified by MPLC eluting with pentane/EtOAc (0-50% gradient) to give ethyl 5-(3-methoxyprop-l-ynyl)-2- phenylthiazole-4-carboxylate as a tan solid (11 g, 88 % yield)
  • 3
  • [ 914347-21-0 ]
  • [ 6089-04-9 ]
  • [ 1231952-94-5 ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 100.0℃; for 0.5h;Inert atmosphere; Microwave irradiation; Nitrogen was bubbled through a solution of Ethyl 5-bromo-2-phenylthiazole- 4-carboxylate (3.6 g, 11.5 mmol) and 2-(prop-2-ynyloxy)tetrahydro-2H-pyran (3.3 rnL, 23.1 mmol) in THF (30 mL). Dichlorobis(triphenylphosphine)palladium (II) (405 mg, 0.6 mmol), copper (I) iodide (55 mg, 0.3 mmol), and triethylamine (TEA) (8 mL, 57.7 mmol) were added and the reaction mixture was heated at 1000C for 30 min in a microwave reactor. The reaction mixture was poured into H2O and extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4), and concentrated. The crude product was purified by MPLC eluting with pentane/EtOAc (0-50% gradient) to give ethyl 2-phenyl-5-(3-(tetrahydro-2H-pyran-2-yloxy)prop-l- ynyl)thiazole-4-carboxylate (3.8 g, 88 % yield)
  • 4
  • [ 914347-21-0 ]
  • (2-(1,3-dioxolan-2-yl)ethyl)zinc(II) bromide [ No CAS ]
  • [ 1231953-00-6 ]
YieldReaction ConditionsOperation in experiment
52% tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; for 16.0h;Reflux; Inert atmosphere; A THF solution of (2-(l,3-dioxolan-2-yl)ethyl)zinc(II) bromide (35 mL. 17.3 mmol) was added to a degassed solution of ethyl 5-bromo-2-phenylthiazole-4- carboxylate (3.6 g, 11.5 mmol) and tetrakistriphenylphosphine palladium (666 mg, 0.58 mmol) in THF (20 mL). The reaction mixture was heated at reflux for 16 h then poured into sat aq NaHCO3. The mixture was extracted with EtOAc, washed with brine, dried (MgSO4), and concentrated. The crude product was purified by MPLC eluting with pentane/EtOAc (0-100% gradient) to give ethyl 5-(2-(l,3-dioxolan-2- yl)ethyl)-2-phenylthiazole-4-carboxylate (2.0 g, 52 % yield).
  • 5
  • [ 100-52-7 ]
  • [ 914347-21-0 ]
 

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