Reaktion #497482

Reaktionsgleichung

N-(4-(3-bromopyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine

2-cyclopenten-1-one

n-methyldicyclohexylamine

→

product

3-(2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyridin-3-yl)cyclopent-2-enone

Lösungsmittel

Dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedegassed
2. 2
   Temperaturthe reaction was heated to 110° C
3. 3
   workup.WAITAfter 36 h
4. 4
   Temperaturthe reaction was cooled to 23° C.
5. 5
   workup.ADDITIONdiluted with EtOAc (150 mL)
6. 6
   Waschenwashed with water (100 mL) and brine (100 mL)
7. 7
   Trocknendried over MgSO4
8. 8
   Einengenconcentrated in vacuo
9. 9
   Sonstigepurified by silica gel chromatography (eluant: 0.5-3% methanol/dichloromethane)

Vorschrift

A solution of N-(4-(3-bromopyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine (600 mg, 1.506 mmol), 2-cyclopenten-1-one (0.609 mL, 7.53 mmol), n-methyldicyclohexylamine (0.959 mL, 4.52 mmol) and bis(tri-tert-butylphosphine)palladium (0) (77 mg, 0.151 mmol) in Dioxane (4 mL) was capped, degassed and backfilled with argon. The reaction was heated to 90° C. After 6 h, the reaction was heated to 110° C. After 36 h, the reaction was cooled to 23° C., diluted with EtOAc (150 mL) and washed with water (100 mL) and brine (100 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluant: 0.5-3% methanol/dichloromethane), affording the product as a yellow solid. MS (ESI, pos. ion) m/z: 400.1 (M+1).

Quelle