Reaktion #156388

Reaktionsgleichung

(rac)-[6-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-yl]-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanol

(rac)-[6-fluoro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-indazol-5-yl]-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanol

iodine

H3PO2

→

title compound

3-(6-Fluoro-1H-indazol-5-ylmethyl)-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere introduced in a microwave tube
2. 2
   SonstigeThe solvent was removed
3. 3
   Waschenwashed with EtOAc three times
4. 4
   Extraktionextracted with EtOAc/MeOH (9:1) three times
5. 5
   Waschenwashed with brine
6. 6
   Trocknendried over Na2SO4
7. 7
   Sonstigethe solvent was removed
8. 8
   SonstigeThe residue was purified by MPLC with DCM and MeOH

Vorschrift

A mixture of (rac)-[6-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-yl]-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanol and (rac)-[6-fluoro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-indazol-5-yl]-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanol (Stage 164.3, 400 mg, 0.810 mmol), iodine (617 mg, 2.431 mmol) and H3PO2 (1.326 mL of a 50% aqueous solution, 12.16 mmol) were introduced in a microwave tube and the mixture was subjected to MW-irradiation at 150° C. for 5 min. The solvent was removed and the residue was taken up with 1 N HCl and washed with EtOAc three times. The aqueous layer was basified with NaOH pellets and extracted with EtOAc/MeOH (9:1) three times. The organics were joined and washed with brine, dried over Na2SO4 and the solvent was removed. The residue was purified by MPLC with DCM and MeOH to give the title compound as a light yellow solid (tR 0.90 min (conditions 2), MH+=348, 1H-NMR in DMSO-d6: 13.00 (s, 1H); 8.40 (s, 1H); 8.05 (m, 2H); 7.75 (d, 1H); 7.55 (m, 2H); 7.32 (d, 1H)).

Quelle