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Chemical Structure| 127406-12-6 Chemical Structure| 127406-12-6

Structure of 127406-12-6

Chemical Structure| 127406-12-6

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Product Details of [ 127406-12-6 ]

CAS No. :127406-12-6
Formula : C10H7NOS
M.W : 189.23
SMILES Code : O=CC1=CC=C(C2=CSC=N2)C=C1
MDL No. :MFCD24678330
InChI Key :WDMCSJWJYXTEJI-UHFFFAOYSA-N
Pubchem ID :15045330

Safety of [ 127406-12-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 127406-12-6 ]

* 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 [ 127406-12-6 ]

[ 127406-12-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 87199-17-5 ]
  • [ 34259-99-9 ]
  • [ 127406-12-6 ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 16h;Reflux; Inert atmosphere; To a solution of <strong>[34259-99-9]<strong>[34259-99-9]4-bromothiazol</strong>e</strong> (see The Journal of Organic Chemistry, 71, 3754 (2006)) (1.31 g, 7.98 mmol) in 1,2-dimethoxyethane (38.0 ml) were added 4-formylphenylboronic acid (1.45 g, 9.67 mmol), sodium hydrogencarbonate (2.00 g, 23.8 mmol) and water (19 ml), which was deaerated under reduced pressure, followed by argon substitution. Tetrakis(triphenylphosphine)palladium (270 mg, 0.234 mmol) was then added, followed by heating to reflux for 16 hours under argon atmosphere. After completion of the reaction, a saturated aqueous sodium chloride solution was added to the reaction solution, followed by extraction with chloroform. The separated organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=4:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.29 g) as a slightly yellow solid. (Yield: 85percent) Mass spectrum (CI, m/z): 190 (M++1). 1H-NMR spectrum (CDCl3, ppm): 10.05 (s, 1H), 8.93 (d, J=2.0Hz, 1H), 8.14-8.10 (m, 2H), 799-7.94 (m, 2H), 7.73 (d, J=2.0Hz, 1H).
85% With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 16h;Inert atmosphere; Reflux; 15-(a) 4-(Thiazol-4-yl)benzaldehyde To a solution of <strong>[34259-99-9]<strong>[34259-99-9]4-bromothiazol</strong>e</strong> (see The Journal of Organic Chemistry, 71, 3754 (2006)) (1.31 g, 7.98 mmol) in 1,2-dimethoxyethane (38.0 ml) were added 4-formylphenylboronic acid (1.45 g, 9.67 mmol), sodium hydrogencarbonate (2.00 g, 23.8 mmol) and water (19 ml), which was deaerated under reduced pressure, followed by argon substitution. Tetrakis(triphenylphosphine)palladium (270 mg, 0.234 mmol) was then added, followed by heating to reflux for 16 hours under argon atmosphere. After completion of the reaction, a saturated aqueous sodium chloride solution was added to the reaction solution, followed by extraction with chloroform. The separated organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=4:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.29 g) as a slightly yellow solid. (Yield: 85percent) Mass spectrum (CI, m/z): 190 (M++1). 1H-NMR spectrum (CDCl3, deltappm): 10.05 (s, 1H), 8.93 (d, J=2.0Hz, 1H), 8.14-8.10 (m, 2H), 7.99-7.94 (m, 2H), 7.73 (d, J=2.0Hz, 1H).
  • 2
  • [ 34259-99-9 ]
  • [ 128376-64-7 ]
  • [ 127406-12-6 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 6h; Pd(dppf)Cl2.CH2Cl2 (0.17 g, 0.0002 mole) was added to a stirred mixture of 4- bromothiazole (0.7 g, 0.004 mol), sodium carbonate ( 1.3 g, 0.012 mole) and 4-(4,4,5,5- tetramethyl-[l,3,2]dioxaborolan-2-yl)benzaldehyde (1.89 g, 0.008 mole) in a mixture of 1,4-dioxane and water (25 mL, 4: 1). The reaction mixture was heated to 80 °C and maintained for 6 hours, cooled to RT, diluted with H20 (10 mL), extracted with ethyl acetate (25 mL x 3). The organic extracts were combined, dried over anhydrous Na2S04 and concentrated under vacuum to obtain the crude 4-(thiazol-4-yl) benzaldehyde that was used as such for further reaction.
 

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