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CAS No. : | 851524-96-4 | MDL No. : | MFCD09907980 |
Formula : | C5H7BN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NPJBPJIQMCHZLJ-UHFFFAOYSA-N |
M.W : | 137.93 | Pubchem ID : | 22396308 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
37% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; water; at 90℃; for 16h;Inert atmosphere; | Monomer Synthesis Procedure A 1-Bromo-3-cyclopropylbenzene (0.20 g, 1.4 mmol, 1.0 eq.), 6- Aminopyridine-3-boronic acid (0.28 g, 1 .4 mmol, 1 .0 eq.) and C52C03 (1 .41g, 4.3 mmol, 1 .5 eq.) were added to a mixture of dioxane (8 mL) and water (2 mL) which was subsequently degassed with argon for 30 mi Pd(PPh3)4 (0.087 g, 4.3 mmol, 0.05 eq.) was added and the reaction mixture was heated to 90 C for 16 h. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated under reducedpressure. The resulting crude material was dissolved in ethyl acetate (100 mL) and washed with cold water (100 mL) and brine (25 mL). The organic layer was dried over Na2504 and concentrated under reduced pressure to obtain crude product. This material was purified by flash chromatography (over silica gel 100-200 mesh) eluting with 25 % ethyl acetate in petroleumether to obtain pure 5-(3-cyclopropylphenyl)pyridin-2-amine (80 mg; 37%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 85℃; for 16h; | To a solution of 4-(5-bromopyrimidin-2-yl)mo holine (5.5 g, 22.53 mmol), (6-aminopyridin-3- yl)boronic acid (5 g, 36.2 mmol), K2C03 (9.34 g, 67.6 mmol) and Pd(PPh3)4 (1.302 g, 1.127 mmol) in 1,4-dioxane (150 mL) and water (75 mL) was heated to about 85 C and stirred for aboutl6 h. The reaction mixture was cooled to rt and filtered. Water was added and a precipitate formed. EtOAc was added and the solid remaining between the phases was collected by filtration, washed with water and EtOAc, and dried under vacuum to give the title compound (3.52 g, 61%). The organic phase from the filtrate was separated and the aqueous phase was extracted once more with EtOAc. The organics were combined, dried over MgSO/i, filtered and concentrated in vacuo to give crude product. The residue was purified by flash-column chromatography on silica gel (2 M NH3 in MeOH/DCM 0-15%) to afford additional title compound (0.69 g, 12%); LC/MS (Table 1, Method e) P = 0.67 min; MS m/z: 258 (M+ H)+ |
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