Tributyltin Chloride → N,N-dimethyl-3-(6-methyl-3-(tributylstannyl)-1H-indazol-1-yl)propan-1-amine

HRID 246678Notes

Reaction equation

I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[N:4]([CH2:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[N:3]=1.C([Mg]Cl)(C)C.[CH2:23]([Sn:27]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:29][CH2:30][CH2:31][CH3:32])Cl)[CH2:24][CH2:25][CH3:26]>C1COCC1>[CH3:16][N:15]([CH3:17])[CH2:14][CH2:13][CH2:12][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=2)[C:2]([Sn:27]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:23][CH2:24][CH2:25][CH3:26])=[N:3]1

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of 3-(3-iodo-6-methyl-1H-indazol1-yl)-N,N-dimethylpropan-1-amine (400 mg, 1.2 mmol) in 20 mL of dry THF was cooled to −20° C. under nitrogen atmosphere, then isopropylmagnesium chloride (1.2 mL, 2.4 mmol, 2M in THF) was added and stirred for 15 min at −20° C. Then tributylchlorostannane (0.7 mL, 2.4 mmol) was added and allowed to warm to room temperature. The reaction was cooled in an ice bath and quenched with saturated ammonium chloride solution, product extracted with ethyl acetate (3×50 mL), combined organics dried with sodium sulfate and concentrated to give N,N-dimethyl-3-(6-methyl-3-(tributylstannyl)-1H-indazol-1-yl)propan-1-amine (1.2 g, crude) as an oil which was used in the next step directly without further purification.

Workup

temperatureto warm to room temperature
temperatureThe reaction was cooled in an ice bath
customquenched with saturated ammonium chloride solution, product
extractionextracted with ethyl acetate (3×50 mL)
dry with materialcombined organics dried with sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-8b6c18f1c09b490093d1001231401444
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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