Reaktion #1616620
ord-7353134da79b4cabbda5d4b6238407bc
Reaktionsgleichung
Edukte
Reaktionsbedingungen
Aufarbeitung
- 1SonstigeA glass microwave reaction vessel
- 2Filtrationfiltered through a plug of celite
- 3Waschenwashed with DCM
- 4WaschenThe filtrate was washed with water (25 mL×3)
- 5Sonstigethe organic layer was dried
- 6Filtrationfiltered
- 7Einengenconcentrated
- 8SonstigeThe residue was purified with silica gel chromatography (eluting with 0-10% EtOAc in Hexanes)
Vorschrift
A glass microwave reaction vessel was charged with 5-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (0.82 g, 2.015 mmol) and 4-((4-methoxybenzyl)oxy)-2-(methylsulfonyl)-6-(trimethylstannyl)pyrimidine (1.013 g, 2.216 mmol) in DMF (5 mL) followed by Pd(PPh3)4 (0.116 g, 0.101 mmol) and CuI (0.017 ml, 0.504 mmol). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 90° C. for 30 min. The mixture was diluted with DCM (5 mL), filtered through a plug of celite and washed with DCM. The filtrate was washed with water (25 mL×3) and the organic layer was dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 0-10% EtOAc in Hexanes) to give 5-bromo-3-(6-((4-methoxybenzyl)oxy)-2-(methylsulfonyl)pyrimidin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (508 mg, 0.886 mmol, 44.0% yield) as a white foam. MS (ESI, pos. ion) m/z: 573/575 (1:1) (M+1); 1H NMR (400 MHz, CDCl3) δ ppm 1.67-1.86 (m, 3 H) 2.06-2.26 (m, 2 H) 2.49-2.64 (m, 1 H) 3.48 (s, 3 H) 3.72-3.80 (m, 1 H) 3.82 (s, 3 H) 3.91-4.01 (m, 1H) 5.52 (s, 2 H) 5.79 (dd, J=8.41, 2.93 Hz, 1 H) 6.93 (m, J=8.80 Hz, 2 H) 7.45 (m, J=8.80 Hz, 2 H) 7.51-7.60 (m, 2 H) 7.70 (s, 1 H) 8.68-8.74 (m, 1 H).