Reaktion #626371

Reaktionsgleichung

water

methyl 2-methyl-5-(4-morpholinyl)-1H-benzimidazole-7-carboxylate

K2CO3

5-(bromomethyl)quinoline

→

product

Ausbeute 24.0%

methyl 2-methyl-6-(4-morpholinyl)-1-(8-quinolinylmethyl)-1H-benzimidazole-4-carboxylate

Ausbeute 24.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   TemperaturThe reaction mixture was cooled
3. 3
   Extraktionextracted with EtOAc (50 mL×3)
4. 4
   TrocknenThe combined organic layers were dried by Na2SO4
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe resulting residue was purified by silica gel chromatography
7. 7
   Wascheneluted with EtOAc
8. 8
   SonstigeMeOH=100:1 to give the crude product (350 mg, 46%), finally it
9. 9
   Sonstigewas purified by Prep-HPLC

Vorschrift

A mixture of methyl 2-methyl-5-(4-morpholinyl)-1H-benzimidazole-7-carboxylate, prepared as described in Example 26, step d (500 mg, 1.82 mmol), K2CO3 (502 mg, 3.64 mmol) and 5-(bromomethyl)quinoline (424 mg, 1.91 mmol) in DMF (25 mL) was stirred at 80° C. for 18 h. The reaction mixture was cooled, poured into water (100 mL) and extracted with EtOAc (50 mL×3). The combined organic layers were dried by Na2SO4 and concentrated. The resulting residue was purified by silica gel chromatography eluted with EtOAc:MeOH=100:1 to give the crude product (350 mg, 46%), finally it was purified by Prep-HPLC to give the product (180 mg, 24%) as a red solid. 1H NMR (300 MHz, DMSO-d6): δ ppm 2.52 (s, 3H), 3.03 (t, 4H, J=4.8 Hz), 3.70 (t, 4H, J=4.8 Hz), 3.88 (s, 3H), 6.08 (s, 2H), 6.87 (d, 1H, J=7.5 Hz), 7.31 (d, 1H, J=2.1 Hz), 7.36 (d, 1H, J=2.1 Hz), 7.48 (t, 1H, J=7.5 Hz), 7.66 (dd, 1H, J=4.2, 8.4 Hz), 7.93 (d, 1H, J=7.5 Hz), 8.44 (dd, 1H, J=1.8, 8.4 Hz), 9.05 (dd, 1H, J=1.8, 4.2 Hz); LC-MS: m/e=417 [M+1]+

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