Tributyltin Chloride → 6-Fluoro-3-methylsulfanyl-1-tributylstannanyl-imidazo[1,5-a]pyridine

HRID 245875Notes

Reaction equation

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

Participants

Conditions

Temperature: -16 °C

Procedure

In a round-bottomed flask, 6-fluoro-1-iodo-3-methylsulfanyl-imidazo[1,5-a]pyridine (109 mg, 0.35 mmol) was dissolved in THF (3 ml). The light brown solution was cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride (2.0 M in THF, 0.21 ml, 0.42 mmol) was added dropwise. The reaction mixture was stirred at −16° C. for 20 min then tributylchlorostannane (0.11 ml, 0.40 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 ethyl acetate (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to give 6-fluoro-3-methylsulfanyl-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 ethyl acetate (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-eea73bedcce548f3ae5c22228bb51116
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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