Tributyltin Chloride → 6-tert-butyl-1-methyl-3-tributylstannanyl-1H-indazole

HRID 246027Notes

Reaction equation

[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([C:9](I)=[N:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[CH2:21]([Sn:25]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])Cl)[CH2:22][CH2:23][CH3:24]>C1COCC1>[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([Sn:25]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:21][CH2:22][CH2:23][CH3:24])=[N:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-tert-butyl-3-iodo-1-methyl-1H-indazole (150 mg, 0.45 mmol) in THF (3 mL) at 0° C. was slowly added isopropylmagnesium chloride (2.0 M in THF, 0.27 mL, 0.54 mmol). The bright yellow heterogeneous reaction mixture was stirred at 0° C. for 1 h then tributylchlorostannane (0.15 mL, 0.54 mmol) was added dropwise. Stirring was continued at 0° C. for 20 min then at room temperature for 3 h. The reaction mixture was quenched with water and extracted with EtOAc (2×). The combined organics were washed with brine then dried over MgSO4 and concentrated to afford 6-tert-butyl-1-methyl-3-tributylstannanyl-1H-indazole as a viscous yellow oil which was used in the next step without further purification.

Workup

customat 0° C.
stirringStirring
waitwas continued at 0° C. for 20 min
waitat room temperature for 3 h
customThe reaction mixture was quenched with water
extractionextracted with EtOAc (2×)
washThe combined organics were washed with brine
dry with materialthen dried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-1c673ba749194d31b97dcc6cd2cd285d
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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