1-methyl-3-(tributylstannyl)-5-(trifluoromethyl)-1H-indazole → methyl 2-(1-methyl-5-(trifluoromethyl)-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate

温度

80 °C

To a solution of methyl 2-bromo-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (300 mg, 0.81 mmol) and 1-methyl-3-(tributylstannyl)-5-(trifluoromethyl)-1H-indazole (396 mg, 0.89 mmol) in DMF (10 mL) were added CuI (30 mg, 0.16 mmol) and Pd(PPh3)4 (47 mg, 0.041 mmol), the reaction mixture was degassed by bubbling nitrogen for 3 minutes and refilled with nitrogen. The mixture was heated to 80° C. for 5 hours under nitrogen, after cooling, water (50 mL) was added to the mixture and product extracted with EtOAc (3×40 mL), the combined organic layers were dried over Na2SO4, concentrated under reduced pressure and the residue was triturated with petroleum ether (2 mL) then decanted and dried to give methyl 2-(1-methyl-5-(trifluoromethyl)-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (280 mg, 70.7%) as an orange solid. LCMS: (M+H)+=490.

1. customthe reaction mixture was degassed
2. customby bubbling nitrogen for 3 minutes
3. additionrefilled with nitrogen
4. temperatureafter cooling
5. additionwater (50 mL) was added to the mixture and product
6. extractionextracted with EtOAc (3×40 mL)
7. dry with materialthe combined organic layers were dried over Na2SO4
8. concentrationconcentrated under reduced pressure
9. customthe residue was triturated with petroleum ether (2 mL)
10. customthen decanted
11. customdried

ORDレコード

ord-79be7dd39f8f4c289aed8a9896229b5c

出典データセット

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08658646B2