Tributyltin iodide → 1-cyclobutyl-6-difluoromethoxy-2-tributylstannanyl-1H-indole-3-carbonitrile

HRID 1028000Notes

Reaction equation

[CH:1]1([N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH:15]([F:17])[F:16])[CH:12]=3)[C:7]([C:18]#[N:19])=[CH:6]2)[CH2:4][CH2:3][CH2:2]1.[CH2:20]([Sn:24](I)([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23].[Li+].CC([N-]C(C)C)C>C1COCC1>[CH:1]1([N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH:15]([F:16])[F:17])[CH:12]=3)[C:7]([C:18]#[N:19])=[C:6]2[Sn:24]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:2][CH2:3][CH2:4]1

Participants

Conditions

Temperature: -78 °C

Procedure

To 1-cyclobutyl-6-difluoromethoxy-1H-indole-3-carbonitrile (830 mg, 3.17 mmol) in THF (10 mL) was added tributyltin iodide (1.13 mL, 4.04 mmol) and the solution cooled to −78° C. A solution of LDA (1.5M in cyclohexane, 3.4 mL, 5.1 mmol) was added dropwise. After complete addition the bath was removed and the mixture stirred at room temperature for 1 hour. THF was then removed under vacuum and the residue filtered through silica gel using CH2Cl2 as an eluant and the mixture concentrated. The residue was purified by flash chromatography using 30-50% CH2Cl2/hexanes to provide 1-cyclobutyl-6-difluoromethoxy-2-tributylstannanyl-1H-indole-3-carbonitrile as a clear, colorless oil (1.23 g, 70%).

Workup

additionAfter complete addition the bath
customwas removed
customTHF was then removed under vacuum
filtrationthe residue filtered through silica gel
concentrationthe mixture concentrated
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-6204be65cd7e449f9062b60d63186818
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735414B2

Reaction notes

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