Reaktion #6951

Reaktionsgleichung

K2CO3

5-[5-(3-hydroxyphenylamino)-2-methyl-phenyl]-2-methylsulfanyl-4-pyridin-3-yl-thiophene-3-carbonitrile

3-bromo-propan-1-ol

→

desired product

Ausbeute 99.0%

5-{5-[3-(3-Hydroxy-propoxy)-phenylamino]-2-methyl-phenyl}-2-methylsulfanyl-4-pyridin-3-yl-thiophene-3-carbonitrile

Ausbeute 99.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepartitioned between water and DCM
2. 2
   ExtraktionThe mixture was extracted with DCM (30 ml×3)
3. 3
   Trocknenthe combined organic layers were dried over Na2SO4
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigePurification by chromatography (2% MeOH-DCM)

Vorschrift

To a solution of 5-[5-(3-hydroxyphenylamino)-2-methyl-phenyl]-2-methylsulfanyl-4-pyridin-3-yl-thiophene-3-carbonitrile (330 mg, 0.77 mmol) in DMF (anhydrous, 5 mL) was added 3-bromo-propan-1-ol (214 mL, 1.54 mmol). The reaction was stirred at 70° C. in the presence of excess K2CO3 overnight then cooled to ambient temperature and partitioned between water and DCM. The mixture was extracted with DCM (30 ml×3) and the combined organic layers were dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (2% MeOH-DCM) afforded desired product (370 mg, 99%). 1H NMR (CDCl3): δ 8.6 (d, 1H), 8.5 (d, 1H), 8.1 (s, 1H), 7.7 (d, 1H), 7.4 (s, 1H), 7.3–7.2 (m, 3H), 7.0 (d, 1H), 6.6 (d, 1H), 4.1 (t, 2H), 3.9 (t, 2H), 2.7 (s, 3H), 2.0 (m, 2H), 1.5 (s, 3H)

Quelle