Reaktion #162543

Reaktionsgleichung

(S)-tert-butyl (1-(2-chloro-7-fluoroquinolin-3-yl)ethyl)carbamate

2-(methylthio)phenylboronic acid

Na2CO3

MeCN

→

(S)-tert-butyl (1-(7-fluoro-2-(2-(methylthio)phenyl)quinolin-3-yl)ethyl)carbamate

Ausbeute 94.8%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to rt
2. 2
   Sonstigethe reaction was partitioned between EtOAc (10 mL) and water (5 mL)
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed
5. 5
   Sonstigedried
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by column chromatography on silica gel

Vorschrift

A mixture of (S)-tert-butyl (1-(2-chloro-7-fluoroquinolin-3-yl)ethyl)carbamate (382 mg, 1.2 mmol), 2-(methylthio)phenylboronic acid (257 mg, 1.3 eq), Na2CO3 (623 mg, 5.0 eq), Pd(PPh3)4 (93 mg, 5%), MeCN (9 mL) and water (3 mL) was heated to 85° C. under N2 overnight. After cooling to rt, the reaction was partitioned between EtOAc (10 mL) and water (5 mL). The organic layer was separated, washed, dried and concentrated. The residue was purified by column chromatography on silica gel to give a white solid (S)-tert-butyl (1-(7-fluoro-2-(2-(methylthio)phenyl)quinolin-3-yl)ethyl)carbamate (460 mg, 94.8%). Mass Spectrum (ESI) m/e=413 (M+1).

Quelle