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CAS No. : | 858116-66-2 | MDL No. : | MFCD08688597 |
Formula : | C16H25BrN2Si | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | UJUSITKTVXDVLQ-UHFFFAOYSA-N |
M.W : | 353.37 | Pubchem ID : | 24229223 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P270-P301+P312-P330-P501 | UN#: | |
Hazard Statements: | H302 | Packing Group: | |
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 |
---|---|---|
6% | With palladium diacetate; sodium t-butanolate; XPhos; In 1,4-dioxane; at 110℃;Inert atmosphere; | An oven dried schlenk flask was evacuated with vacuum and back filled with argon gas. The procedure was repeated for 3-4 times and cooled to room temperature. The dioxane (3 ml) was introduced with syringe and degassed for 20 min with argon gas balloon. Then, the XPhos (80 mg, 0.168mmol), Pd(OAc)2 (12mg, 0.056 mmol) were added together and heated at 110 C for 1minute. The reaction mixtures become clear red color solution. Then, the amine derivative 5 (75 mg, 0.56 mmol), 5-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (200 mg, 0.56 mmol) and sodium tert-butoxide (160 mg, 1.68 mmol) were added together under argon atmosphere and the reaction mixture was heated at 110 C for 1h. The reaction mixture was poured in EtOAc (200 ml). The organic phase was washed with water, brine, and dried over Na2SO4. The solvent was removed and the residue was purified on silica gel column chromatography (20:80 EtOAc: Hept) to give compound 44a (17mg, 6%). 1H-NMR (400 MHz, CDCl3): delta = 8.37 (d, J = 2.0Hz, 1H), 8.04 (d, J = 2.4Hz, 1H), 7.75 (d, J = 8.4Hz, 1H), 7.32 (d, J = 3.2Hz, 1H), 7.01 (s, 1H), 6.96 (brs, 1H), 6.59 (d, J = 8.4 Hz, 1H) 6.52 (d, J = 3.6Hz, 1H) 6.41(brs, 1H), 6.37(dd, J = 1.6Hz, J=3.2Hz, 1H), 1.90 (m 3H), 1.16 (d, J = 7.6Hz, 18H). |