Tributyltin Chloride → 1-methyl-3-tributylstannanyl-1H-indazole-5-carbonitrile

HRID 246293Notes

Reaction equation

I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[N:4]([CH3:13])[N:3]=1.C([Mg]Cl)(C)C.[CH2:19]([Sn:23]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])Cl)[CH2:20][CH2:21][CH3:22]>C1COCC1>[CH3:13][N:4]1[C:5]2[C:10](=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=2)[C:2]([Sn:23]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:19][CH2:20][CH2:21][CH3:22])=[N:3]1

Participants

Conditions

Temperature: -16 °C

Procedure

In a round-bottomed flask, 3-iodo-1-methyl-1H-indazole-5-carbonitrile (383 mg, 1.35 mmol) was partially dissolved in THF (10 ml). The light yellow suspension was cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride (2.0 M in THF, 0.82 ml, 1.64 mmol) was added dropwise. The reaction mixture was stirred at −16° C. for 30 min then tributylchlorostannane (0.43 ml, 1.59 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirred for 1.5 h then quenched with saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to provide 1-methyl-3-tributylstannanyl-1H-indazole-5-carbonitrile as a brown oil which was used without further purification.

Workup

additionwas added dropwise
temperatureto warm to room temperature
stirringstirred for 1.5 h
customthen quenched with saturated aqueous NH4Cl
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-0ff1e79b67174db4803e4a16bbb80af0
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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