Tributyltin Chloride → 6-chloro-1-methyl-3-tributylstannanyl-1H-indazole

HRID 245793Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](I)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[CH2:18]([Sn:22]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:24][CH2:25][CH2:26][CH3:27])Cl)[CH2:19][CH2:20][CH3:21]>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([Sn:22]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:18][CH2:19][CH2:20][CH3:21])=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -16 °C

Procedure

6-Chloro-3-iodo-1-methyl-1H-indazole (108 mg, 0.35 mmol) was dissolved in THF (2 ml) and the solution was cooled to −16° C. using a NaCl/ice bath. Isopropylmagnesium chloride (2.0M in THF, 0.20 ml, 0.40 mmol) was added dropwise and the reaction mixture was stirred at −16° C. for 15 min. Tributylchlorostannane (0.11 ml, 0.40 mmol) was slowly added and the reaction mixture was allowed to warm to room temperature over 1.5 h. The reaction mixture was quenched with saturated NH4Cl solution and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to afford 6-chloro-1-methyl-3-tributylstannanyl-1H-indazole as a brown oil which was used without further purification.

Workup

temperatureto warm to room temperature over 1.5 h
customThe reaction mixture was quenched with saturated NH4Cl solution
extractionextracted with EtOAc (2×)
washThe combined organic layers were washed with water and brine
dry with materialthen dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-e4c31799a46b451fabf2a3c8689a1638
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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