Dibutylchloro(propyl)stannane → 5-(Difluoromethoxy)-1-methyl-3-(tributylstannyl)-1H-indazole

To a solution of 5-(difluoromethoxy)-3-iodo-1-methyl-1H-indazole (400 mg, 1.23 mmol) in dry THF (15 mL) was added isopropylmagnesium chloride (0.75 mL, 1.3 mmol, 2M in THF) drop-wise at −16° C. under nitrogen atmosphere, stirred for 30 minutes, then dibutylchloro(propyl)stannane (0.5 mL, 1.45 mmol) was added drop-wise, the reaction mixture was warmed to room temperature slowly and stirred for 2 hours. The reaction mixture was quenched with a saturated solution of NH4Cl (40 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure and the residue was used into the next step without purification (500 mg, crude) as oil.

1. stirringstirred for 2 hours
2. customThe reaction mixture was quenched with a saturated solution of NH4Cl (40 mL)
3. extractionextracted with EtOAc (3×30 mL)
4. dry with materialThe combined organic layers were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customthe residue was used into the next step without purification (500 mg, crude) as oil

ORD-Eintrag

ord-e3d12928dbe341bb81bba19fe3bc89ef

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08658646B2