Reaktion #167442

Reaktionsgleichung

MeOH

1-(4-chloro-thieno[3,2-c]pyridin-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

1-(4-Chloro-thieno[3,2-c]pyridin-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

methyl boronic acid

potassium carbonate

→

product

Ausbeute 16.4%

4-Methyl-pyridin 3-(4-methyl-thieno[3,2-c]pyridin-2-yl)-imidazolidin-2-one

Ausbeute 16.4%

Lösungsmittel

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepreviously purged with argon (30 minutes)
2. 2
   SonstigeThe reaction mixture was purged with argon for 15 minutes
3. 3
   TemperaturThe reaction mixture was heated
4. 4
   Temperaturto reflux for 6 hours
5. 5
   EinengenThe reaction mixture was concentrated
6. 6
   Sonstigeto afford the crude product
7. 7
   SonstigePurification by column chromatography on silica gel (3-4% MeOH in CHCl3)

Vorschrift

Tetrakis (triphenylphosphine) palladium (33 mg, 0.0288 mmol) was added to potassium carbonate (120 mg, 0.8649 mmol) previously purged with argon (30 minutes). The reaction mixture was purged with argon for 15 minutes, followed by the addition of 1-(4-chloro-thieno[3,2-c]pyridin-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (98A: 100 mg, 0.2883 mmol) and methyl boronic acid (21 mg, 0.3459 mmol). The reaction mixture was heated to reflux for 6 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was concentrated to afford the crude product. Purification by column chromatography on silica gel (3-4% MeOH in CHCl3), followed by preparative HPLC afforded 10 mg of the product (16.39% yield).

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