Cesium carbonate → 3-(4-Chlorophenyl)-N-(2,2-dimethyl-propyl)-1-[(4-fluorophenyl)-methyl]-N-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acid amide

온도

60 °C

To a solution of 3-(4-chlorophenyl)-N-methyl-N-neopentyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxamide (100 mg, 0.268 mmol) in dry DMF (1.5 mL) was added 1-(bromomethyl)-4-fluorobenzene (35 μL, 0.282 mmol) and Cs2CO3(131 mg, 0.402 mmol). The white suspension was stirred at 60° C. for 1 h. The reaction mixture was poured out in saturated aqueous NaHCO3 (25 mL) and the product was extracted with EtOAc (2×25 mL). The combined organic layers were washed with saturated aqueous NaHCO3 (2×15 mL), aqueous 1M KHSO4 (2×15 mL) and brine (2×15 mL) before drying on Na2SO4 and concentration in vacuo. The product was purified using flash chromatography (silica, gradient heptane/EtOAc 95:5→7:3). The product containing fractions were combined, concentrated in vacuo and crystallised from hot i-Pr2O to give a first batch of SC-261. The mother liquor was concentrated in vacuo and crystallised from i-Pr2O/heptane (1:1) to give white crystals which were combined with the earlier obtained batch to give SC-261 (58 mg, 45%) as colorless crystals.

1. extractionthe product was extracted with EtOAc (2×25 mL)
2. washThe combined organic layers were washed with saturated aqueous NaHCO3 (2×15 mL), aqueous 1M KHSO4 (2×15 mL) and brine (2×15 mL)
3. custombefore drying on Na2SO4 and concentration in vacuo
4. customThe product was purified
5. additionThe product containing fractions
6. concentrationconcentrated in vacuo
7. customcrystallised from hot i-Pr2O

ORD 기록

ord-a4908847e8d1428d97f304ffd5a94855

출처 데이터셋

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09302988B2