Reaktion #597451

Reaktionsgleichung

(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate

5-methoxy-3-pyridineboronic acid pinacol ester

potassium carbonate

→

(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(5′-methoxy-2,3′-bipyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeflushed with argon three times
2. 2
   workup.ADDITIONTo this mixture was added
3. 3
   Sonstigedegassed 1,4-dioxane (0.8 mL) and water (0.2 mL)
4. 4
   Temperaturthen cooled to rt
5. 5
   SonstigeThe aqueous layer was separated
6. 6
   Extraktionextracted three times with ethyl acetate
7. 7
   Trocknendried over Na2SO4
8. 8
   Einengenconcentrated
9. 9
   SonstigePurification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent)
10. 10
    Sonstigeprovided the product

Vorschrift

(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate (40.0 mg, 0.070 mmol), 5-methoxy-3-pyridineboronic acid pinacol ester (19.7 mg, 0.084 mmol), potassium carbonate (29.0 mg, 0.210 mmol), and Pd(PPh3)4 (12.1 mg, 0.010 mmol) were placed in a microwave vial and the vial was vacuum pumped and flushed with argon three times. To this mixture was added degassed 1,4-dioxane (0.8 mL) and water (0.2 mL). The reaction mixture was heated at 110° C. for 1 h then cooled to rt. The aqueous layer was separated and extracted three times with ethyl acetate. All organic layers were combined, dried over Na2SO4, and concentrated. Purification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent) provided the product. LCMS-ESI+: calc'd for C36H39ClN3O4S: 644.2 (M+H+); Found: 644.1 (M+H+); 1H NMR (400 MHz, CDCl3) δ 8.89 (s, 1H), 8.81 (d, J=4.9 Hz, 1H), 8.40 (d, J=2.7 Hz, 1H), 8.35 (s, 1H), 8.02 (s, 1H), 7.95 (s, 1H), 7.83 (d, J=5.2 Hz, 1H), 7.57 (d, J=8.4 Hz, 1H), 7.51 (d, J=8.5 Hz, 1H), 7.43 (d, J=8.4 Hz, 1H), 7.31 (d, J=8.7 Hz, 1H), 4.83 (dd, J=9.4, 2.7 Hz, 1H), 4.43 (dd, J=11.2, 9.5 Hz, 1H), 4.30 (dd, J=12.1, 2.9 Hz, 1H), 3.99 (s, 3H), 2.81 (s, 3H), 1.15 (s, 9H), 0.97 (s, 9H).

Quelle