Reaktion #1071063

Reaktionsgleichung

{3-[4-(4-phenoxy-quinazolin-6-yl)-benzyl}-3-aza-bicyclo[3.1.0]hex-6-yl)-methanol

1-cyclopropylmethyl-1H-indol-5-ylamine

pyridinium hydrochloride

phenol

→

compound 18

Ausbeute 67.0%

(3-{4-[4-(1-Cyclopropylmethyl-1H-indol-5-ylamino)-quinazolin-6-yl]-benzyl}-3-aza-bicyclo[3.1.0]hex-6-yl)methanol

Ausbeute 67.0%

Lösungsmittel

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe vial was capped
2. 2
   TemperaturThe vial was cooled to room temperature
3. 3
   Waschenwashed with 15% aqueous NaOH, water, brine
4. 4
   Trocknendried (MgSO4)
5. 5
   SonstigeThe solvent was removed
6. 6
   Sonstigethe residue purified by flash chromatography (silica gel, EtOAc:MeOH, 95:5)

Vorschrift

To a 3 mL Wheaton vial was added {3-[4-(4-phenoxy-quinazolin-6-yl)-benzyl}-3-aza-bicyclo[3.1.0]hex-6-yl)-methanol 16 (100 mg, 0.24 mmol), 1-cyclopropylmethyl-1H-indol-5-ylamine 19 (48 mg, 0.26 mmol), pyridinium hydrochloride (33 mg, 0.284 mmol), and phenol (155 mg, 1.652 mmol). The vial was capped and heated overnight at 110° C. The vial was cooled to room temperature and the residue taken up in CHCl3 and washed with 15% aqueous NaOH, water, brine, and dried (MgSO4). The solvent was removed and the residue purified by flash chromatography (silica gel, EtOAc:MeOH, 95:5) to provide compound 18 (88 mg, 0.159 mmol) as a light brown solid in 67% yield. For compound 18: MS (Cl) m/e 515 (M++1, 100); HPLC, rt=4.83 min.

Quelle