Water → HCID 86712654, Verbindung

Temperatur

0 °C

To a solution of 2-(5-fluoro-2-((trimethylsilyl)ethynyl)phenyl)acetamide (A34) (0.239 g, 0.958 mmol) in DCM (10 mL) at 0° C. was added TBAF (1.0 M in THF; 1.44 mL, 1.44 mmol). The resulting mixture was stirred at 0° C. for 10 minutes, then poured into water (50 mL). The organic phase was separated and the aqueous layer was extracted with DCM (2×50 mL). The combined organic layers were washed with brine, dried (MgSO4) and the volatiles removed in vacuo. The residue was adsorbed onto silica gel then purified by column chromatography (Biotage Isolera, SiO2, 0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A35 as a white solid (0.114 g, 67%); 1H NMR (400 MHz, d6-DMSO) δ 7.50 (dd, J=8.6, 5.9 Hz, 1H), 7.44 (s, 1H), 7.17 (dd, J=10.0, 2.7 Hz, 1H), 7.10 (td, J=8.6, 2.8 Hz, 1H), 6.99 (s, 1H), 4.32 (s, 1H), 3.61 (s, 2H). LCMS-A: rt 4.843 min; m/z 178 [M+H]+.

1. customThe organic phase was separated
2. extractionthe aqueous layer was extracted with DCM (2×50 mL)
3. washThe combined organic layers were washed with brine
4. dry with materialdried (MgSO4)
5. customthe volatiles removed in vacuo
6. customthen purified by column chromatography (Biotage Isolera, SiO2, 0-100% EtOAc in petroleum benzine 40-60° C.)

ORD-Eintrag

ord-267e14ca25ae4e278b5b6cba922ba8b3

Quelldatensatz

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09266864B2