反应详情

温度

80 °C

To a stirred mixture of 9-Bromo-4-methoxycarbonylmethyl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (90 mg, 0.22 mmol) in TEA (5 mL) and DMF (1 mL) were added Pd(PPh3)Cl2 (15 mg, 0.021 mmol), PPh3 (17.2 mg, 0.065 mmol), CuI (8.3 mg, 0.043 mmol) and 2-methylbut-3-yn-2-ol (92 mg, 1.09 mmol). The reaction mixture was degassed with N2 and heated to 80° C. in a microwave reactor for 1.5 h. Then the mixture was cooled to room temperature, EtOAc was added. The mixture was filtered through Celite. The filtrate was washed with saturated brine, dried over Na2SO4, filtered, concentrated in vacuo, and purified by flash column chromatography (silica gel, EtOAc in hexane from 10% to 20%) to afford 9-(3-Hydroxy-3-methyl-but-1-ynyl)-4-methoxycarbonylmethyl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (70 mg, 77%) as a light yellow solid. LC-MS (ESI & APCI): 416.7 (M+1).

1. customThe reaction mixture was degassed with N2
2. temperatureThen the mixture was cooled to room temperature
3. additionEtOAc was added
4. filtrationThe mixture was filtered through Celite
5. washThe filtrate was washed with saturated brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. custompurified by flash column chromatography (silica gel, EtOAc in hexane from 10% to 20%)