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CAS No. : | 381247-99-0 | MDL No. : | MFCD08235247 |
Formula : | C7H6BrNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KKMVACLRBBJYIJ-UHFFFAOYSA-N |
M.W : | 232.03 | Pubchem ID : | 2764315 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-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 |
---|---|---|
77% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 1h;Inert atmosphere; | To a solution of 36 (0.626 g, 2.70 mmol) in dry THF (35 mL) under anhydrous conditions was added (R)-tent-butyl 3-hydroxypyrrolidine-1-carboxylate (0.505 g, 2.70 mmol) and triphenyl phosphine (1.43 g, 5.39 mmol). The reaction mixture was then cooled in an ice bath, and DIAD (1.12 g, 5.56 mmol) dissolved in THF (10 mL) was added dropwise. The reaction mixture was stirred for 1 h at room temperature under argon. Upon completion the reaction was diluted with ethyl acetate (100 mL). The organic layer was washed with water (2×50 ml), brine (50 mL), dried over MgSO4, solids filtered, and the solvent removed under reduced pressure. The residue was then purified by column chromatography (silica gel, hexanes:EtOAc=7:1) to yield 37 (0.837 g, 77% yield) as white solid. 1H NMR (500 MHz, CDCl3): δ ppm 8.70 (d, 1H, J=2.0 Hz), 8.38 (d, 1H, J=2.1 Hz), 5.64-5.62 (m, 1H), 3.91 (s, 3H), 3.72-3.69 (m, 1H), 3.59-3.52 (m, 3H), 2.21-2.17 (m, 2H), 1.46 (s, 9H). 13C NMR (125 MHz, CDCl3): δ ppm 164.65, 161.64, 154.51, 147.88, 142.55, 121.08, 107.19, 79.47, 72.19, 52.30, 51.65, 44.02, 28.49. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 80℃;Inert atmosphere; Sealed tube; | Pd(PPh3)2Cl2 (12.5 mg, 0.0177 mmol) was added to a nitrogen flushed mixture of methyl 5- bromo-6-hydroxynicotinate (82.1 mg, 0.354 mmol), 4-isopropylphenylacetylene (77 mg, 0.531 mmol), and Cul (6.7 mg, 0.0354 mmol) in Et3N (1 ml). The mixture was heated in at 80 C overnight in a sealed vial. Solvent was evaporated and the crude material purified by flash chromatography using 10-20%) EtOAc in hexanes as eluent. Yield: 6.0 mg (6%>); white solid. Freshly prepared hydroxylamine potassium salt solution (ca 1.7 M in MeOH, 1.5 ml) was added the product from above and the mixture was heated at 60 C for 1 h before quenching with AcOH (0.5 ml). The title compound was isolated by reversed phase chromatography (Kinetex C18, 5 muiotaeta, 21.2 x 100 mm, flow 25 ml/min, gradient 0.1% TFA in water / acetonitrile over 15 minutes). Yield: 2.0 mg (33%); white solid. |