Tributyltin Chloride → 6-Methyl-1-tributylstannanyl-imidazo[1,5-a]pyridine

HRID 245843Notes

Reaction equation

I[C:2]1[N:3]=[CH:4][N:5]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=12.C([Mg]Cl)(C)C.[CH2:17]([Sn:21]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])Cl)[CH2:18][CH2:19][CH3:20]>C1COCC1>[CH3:11][C:9]1[CH:8]=[CH:7][C:6]2[N:5]([CH:4]=[N:3][C:2]=2[Sn:21]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:17][CH2:18][CH2:19][CH3:20])[CH:10]=1

Participants

Conditions

Temperature: -16 °C

Procedure

In a round-bottomed flask, 1-iodo-6-methyl-imidazo[1,5-a]pyridine (97 mg, 0.38 mmol) was dissolved in THF (3 ml). The solution was cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride (2.0M solution in THF, 0.23 ml, 0.46 mmol) was added dropwise. The reaction mixture was stirred at −16° C. for 20 min then tributylchlorostannane (0.12 ml, 0.44 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirred for 2 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 6-methyl-1-tributylstannanyl-imidazo[1,5-a]pyridine as a brown oil which was used without further purification.

Workup

additionwas added dropwise
temperatureto warm to room temperature
stirringstirred for 2 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-1feed4ef5c28412c9eab9b2e58484143
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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