反应详情

To a round-bottomed flask were added 4-[(4-bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol (14) (0.127 g, 0.32 mmoL), 1-N-BOC-pyrrole-2-boronic acid (0.21 g, 1.0 mmoL), tetrakis(triphenylphosphine)palladium (0) (0.033 g, 0.029 mmoL), 2 M Na2CO3 (3 mL), and ethylene glycol dimethyl ether (8 mL). The stirred reaction mixture was heated at reflux overnight under a nitrogen atmosphere. The oil bath was removed and the reaction mixture was allowed to cool at RT. The reaction mixture was transferred to a separatory funnel and partitioned between H2O and EtOAc. The organic phase was separated, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo to give an orange-brown oil. The crude product was purified by flash chromatography on silica gel with a hexanes:EtOAc gradient (100:0 to 80:20) to give 111 mg (72%) of compound 18 as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 0.88 (s, 12 H), 1.24 (m, 11 H), 1.92 (s, 2 H), 1.94 (s, 2 H), 6.19 (m, 1 H), 6.23 (m, 1 H), 6.65 (d, J=8.5 Hz, 2 H), 6.92 (d, J=8.4 Hz, 2 H), 7.09 (d, J=8.1 Hz, 2 H), 7.21 (d, J=8.0 Hz, 2 H), 7.31 (m, 1 H), 9.27 (s, 1 H). LCMS (ESI): m/z 508 (M+Na)+.

1. customThe stirred reaction mixture
2. temperaturewas heated
3. temperatureat reflux overnight under a nitrogen atmosphere
4. customThe oil bath was removed
5. customThe reaction mixture was transferred to a separatory funnel
6. custompartitioned between H2O and EtOAc
7. customThe organic phase was separated
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationthe filtrate was concentrated in vacuo
11. customto give an orange-brown oil
12. customThe crude product was purified by flash chromatography on silica gel with a hexanes