Phosphorus oxychloride → 4-Chloropyrrolo(2,1-f)(1,2,4)triazine

Temperature

100 °C

To a solution of pyrrolo[2,1-f][1,2,4]triazin-4-ol (3.70 g, 27.4 mmol, see generally, PCT Appi. WO 2000/071129 the disclosure of which is herein incorporated by reference in its entirety) in 40 mL of toluene at room temperature was added 4.77 mL (27.4 mmol) of diisopropylethylamine followed by 7.70 mL (82.6 mmol) of phosphorus oxychloride. The reaction mixture was heated at 100° C. for 18 h. After cooling to room temperature, the reaction was slowly added to a solution of 5% aq NaHCO3 solution (100 mL) at 0° C. Upon completion of the addition, the biphasic mixture was allowed to stir at room temperature for 30 min. The aqueous layer was extracted with EtOAc (3×100 mL) and the pooled organic extracts were washed with brine (100 mL), dried over anhydrous MgSO4, and concentrated in vacuo to give the crude product (4.10 g, 97%) as a yellow solid. 1H NMR (CDCl3) δ 8.14 (s, 1H), 7.80 (dd, 1H, J=2.4, 1.5 Hz), 6.91 (m, 2H).

1. customat room temperature
2. temperatureAfter cooling to room temperature
3. additionUpon completion of the addition
4. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
5. washthe pooled organic extracts were washed with brine (100 mL)
6. dry with materialdried over anhydrous MgSO4
7. concentrationconcentrated in vacuo

ORD record

ord-0dde67a72d7b492788ca16afcf83d3ae

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439246B2