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

HRID 246732

Reaction equation

[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[N:13]=[C:12]2I)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[CH2:25]([Sn:29]([CH2:35][CH2:36][CH2:37][CH3:38])([CH2:31][CH2:32][CH2:33][CH3:34])Cl)[CH2:26][CH2:27][CH3:28]>C1COCC1>[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[N:13]=[C:12]2[Sn:29]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:25][CH2:26][CH2:27][CH3:28])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -20 °C

Procedure

The solution of 5-(tert-butyldimethylsilyloxy)-3-iodo-1-methyl-1H-indazole (3.8 g, 10 mmol) in 30 mL of dry THF was cooled to −20° C. under nitrogen, isopropylmagnesium chloride (6 mL, 12 mmol, 2M in THF) was added and stirred for 15 min at −20° C. Tributylchlorostannane (12 mL, 14 mmol) was added and the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The mixture was quenched with saturated solution of ammonium chloride, extracted with ethyl acetate (3×50 mL), dried over sodium sulfate and concentrated to give 5-(tert-butyldimethylsilyloxy)-1-methyl-3-(tributylstannyl)-1H-indazole (5.2 g, crude) as a colourless oil, which was used directly in the next step without further purification.

Workup

temperatureto warm to room temperature
stirringstirred for 1 h
customThe mixture was quenched with saturated solution of ammonium chloride
extractionextracted with ethyl acetate (3×50 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-3d960b5cf7474d26b5e0fba2c9e1ffa1
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Linked notes

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