反应详情

温度

-20 °C

LDA (6.20 mmol) was added dropwise to a solution of 5-bromo-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (Step D4) (2.066 mmol) in THF (15 mL) at −78° C. and the mixture was stirred for 2 h. A solution of 4-chlorobenzaldehyde [104-88-1] (6.20 mmol) in THF (5 mL) was added and the mixture was stirred for 1 h. The mixture was warmed to −20° C., quenched with HOAc and stirred at rt overnight. The reaction mixture was diluted with H2O and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as an off-white solid. tR: 5.57 min (HPLC 1); ESI-MS: tR=1.36 min, [M+H]+ 368/370/372 (LC-MS 1); TLC: Rf=0.23 (1:6 EtOAc/heptanes).

1. stirringthe mixture was stirred for 1 h
2. customquenched with HOAc
3. stirringstirred at rt overnight
4. additionThe reaction mixture was diluted with H2O
5. extractionextracted with EtOAc (3×)
6. washThe combined organic layers were washed with brine
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified