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CAS No. : | 1044851-76-4 | MDL No. : | MFCD07777079 |
Formula : | C9H15BN2O2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | GJNNJJRONITJEY-UHFFFAOYSA-N |
M.W : | 194.04 | Pubchem ID : | 44119444 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 | UN#: | |
Hazard Statements: | H302-H312-H332 | Packing Group: | |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃; for 18h;Sealed tube; | To a solution of methyl 4-bromothiophene-2-car- boxylate (1.00 g, 4.52 mmol) in dioxane/H20 (30:3 mE) was added K2C03 (2.69 g, 19.45 mmol), tetrakistriphenylphosphine Pd(O) (0.78 g, 0.678 mmol), and 5-(5,5-dimethyl-1, 3,2-dioxaborinan-2-yl)-1 -methyl-i H-pyrazole (2.68 g,12.89 mmol). The reaction mixture was heated to 80 C. in a sealed tube for 18 h. The reaction solution was concentrated under vacuum and purified on silica gel (hexanes/ EtOAc, 4:1) to give the title compound methyl 4-(i-methyl- 1H-pyrazol-5-yl)thiophene-2-carboxylate (1.01 g, 100%) as yellow solid. ?H NMR (400 MHz, DMSO-d): oe 8.16 (d, 1H, J=i.6 Hz), 8.02 (d, 1H, J=i.6 Hz), 7.44 (d, 1H=2.0 Hz), 6.56 (d, 1H, J=2.0 Hz), 3.93 (s, 3H), 3.85 (s, 3H); MS (ESI):Calcd, for C1OH1ON2O2S: 222.1, found 223.1 (M+i). |
With potassium carbonate;bis(tri-t-butylphosphine)palladium(0); In 1,4-dioxane; water; at 80℃; for 1h; | To a solution of <strong>[62224-16-2]methyl 4-bromo-2-thiophenecarboxylate</strong> (1 g, 4.52 mmol) in dioxane/H2O (5:1 , 16 ml.) was added K2CO3 (2.7 g, 19 mmol), bis(tri-t- butylphosphine)palladium(O) (116 mg, 0.226 mmol) and 5-(5,5-dimethyl-1 ,3,2- dioxaborinan-2-yl)-1-methyl-1 H-pyrazole (1.2 g, 5.88 mmol). The reaction mixture was heated to 80 C in a sealed tube. After 1 h, the reaction was partitioned <n="136"/>between H2O-DCM and the aqueous phase was extracted several times with DCM. The combined organic fractions were dried over Na2SO4, concentrated and used directly: LCMS (ES) m/z 223 (M+H)+. |