反应详情

温度

100 °C

2-Amino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester (400 mg, 1.16 mmol) and 1-methyl-2-tributylstannanyl-1H-pyrrole (643 mg, 1.5 equiv) were weighed in air and added in a flame-dried flask. [Bistriphenylphosphine]dichloropalladium (124.5 mg, 0.15 equiv) was added and the flask was closed by a septum. Dioxane (16 mL) was added and the mixture was stirred for 1 h (TLC control) at 100° C. After 1 h, 1-methyl-2-tributylstannyl-1H-pyrrole (429 mg, 1 equiv) was added and the mixture was stirred for 35 h (TLC control) at 100° C. The solvent was removed in vacuo, the residue was taken in DCM and washed with a saturated solution of NaHCO3, water and brine. The organic phase was dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography (hexanes to EtOAc/hexanes (4:6)) to furnish 2-amino-5-(1-methyl-1H-pyrrol-2-yl)-4-trifluoromethyl-benzoic acid methyl ester (50 mg, 14.5%) as a yellow oil. ESI-MS: m/z 299 [M+H]+, rt 5.78 min.

1. additionadded in a flame-dried flask
2. customthe flask was closed by a septum
3. waitAfter 1 h
4. stirringthe mixture was stirred for 35 h (TLC control) at 100° C
5. customThe solvent was removed in vacuo
6. washwashed with a saturated solution of NaHCO3, water and brine
7. dry with materialThe organic phase was dried over Na2SO4
8. customevaporated to dryness
9. customThe crude product was purified by flash chromatography (hexanes to EtOAc/hexanes (4:6))