Tributyltin Chloride → 5-isopropyl-1-methyl-3-(tributylstannyl)-1H-indazole

HRID 246768Notes

Reaction equation

I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]([CH3:13])[CH3:12])[CH:9]=2)[N:4]([CH3:14])[N:3]=1.C([Mg]Cl)(C)C.[CH2:20]([Sn:24]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:26][CH2:27][CH2:28][CH3:29])Cl)[CH2:21][CH2:22][CH3:23]>C1COCC1>[CH:11]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([CH3:14])[N:3]=[C:2]2[Sn:24]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:20][CH2:21][CH2:22][CH3:23])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: -16 °C

Procedure

To a stirred solution of 3-iodo-5-isopropyl-1-methyl-1H-indazole (0.3 g, crude) in 100 mL of dry THF at −16° C. under nitrogen was added i-PrMgCl (0.69 mL, 1.38 mmol, 2M in THF) drop-wise. Then the mixture was stirred at −16° C. for 20 minutes. Tributylchlorostannane (0.39 g, 1.2 mmol) was added slowly and the mixture was stirred at room temperature for 2.5 hours. The solution was quenched by 40 mL of water, extracted with ethyl acetate (2×100 mL), washed with water (2×50 mL), brine (50 mL) and dried over anhydrous sodium sulfate. The drying agent was removed by filtration and the filtrate was evaporated under reduced pressure to give crude 5-isopropyl-1-methyl-3-(tributylstannyl)-1H-indazole as an oil, which was used into next step without further purification.

Workup

stirringthe mixture was stirred at room temperature for 2.5 hours
customThe solution was quenched by 40 mL of water
extractionextracted with ethyl acetate (2×100 mL)
washwashed with water (2×50 mL), brine (50 mL)
dry with materialdried over anhydrous sodium sulfate
customThe drying agent was removed by filtration
customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-f1b1c0a617c5455eb71e5632e3fd3250
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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