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

HRID 246325Notes

Reaction equation

I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH3:15])[N:3]=1.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>[CH3:14][S:11]([C:7]1[CH:6]=[C:5]2[C:10]([C:2]([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:3][N:4]2[CH3:15])=[CH:9][CH:8]=1)(=[O:13])=[O:12]

Participants

Conditions

Temperature: -16 °C

Procedure

In a round-bottomed flask, 3-iodo-6-methanesulfonyl-1-methyl-1H-indazole (120 mg, 0.36 mmol) was dissolved in THF (2 ml). The colorless solution was cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride (2.0 M in THF, 0.25 ml, 0.50 mmol) was added dropwise. The reaction mixture was stirred at −16° C. for 1 h then tributylchlorostannane (0.12 ml, 0.44 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature over 2.5 h then 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-methanesulfonyl-1-methyl-3-tributylstannanyl-1H-indazole as a light yellow oil which was used without further purification.

Workup

additionwas added dropwise
temperatureto warm to room temperature over 2.5 h
customthen 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-a16565b00bac42ac9e9ca31e6cc7f466
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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