反应详情

温度

0 °C

To a solution of 3-phenyl-1-(toluene-4-sulfonyl)-1H-indole-2-carbaldehyde (2.11 g, 5.62 mmol) in THF (30 mL) cooled to −78° C. and under a nitrogen atmosphere, was added 3.0M MeMgBr in diethyl ether (2.6 mL). The mixture was stirred at 0° C. for 30 min and then additional 3.0M MeMgBr in diethyl ether (0.3 mL) was added. After 15 min stirring, the reaction mixture was poured into a saturated solution of NH4Cl and extracted with EtOAc (×2). The combined organic layers were washed with water, then dried (Na2SO4) and concentrated in vacuo. The crude material was combined with a second portion of crude reaction mixture obtained following the same method (starting from 140 mg, 3.73 mmol of 3-phenyl-1-(toluene-4-sulfonyl)-1H-indole-2-carbaldehyde) and the combined batches were purified by column chromatography (Si—PCC, gradient 20-100% DCM in pentane) affording the title compound as a gum which then solidified on standing (2.02 g, 86%). 1H NMR (CDCl3, 400 MHz): δ 8.07 (1H, d, J=8.35), 7.80-7.75 (2H, m), 7.51-7.38 (5H, m), 7.33-7.26 (2H, m), 7.20-7.14 (3H, m), 5.25-5.15 (1H, m), 4.06 (1H, d, J=11.01 Hz), 2.31 (3H, s), 1.70 (3H, d, J=6.88 Hz).

1. stirringAfter 15 min stirring
2. extractionextracted with EtOAc (×2)
3. washThe combined organic layers were washed with water
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated in vacuo
6. customreaction mixture
7. customobtained
8. customthe combined batches were purified by column chromatography (Si—PCC, gradient 20-100% DCM in pentane)