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

HRID 1028000
Notes
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Reaction equation

HRID 1028000 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 23765Tributyltin iodideHCID 2724682Lithium diisopropylamideHCID 667306391-cyclobutyl-6-(difluoromethoxy)-1H-indole-3-carbonitrile

Product 1

HCID 667305741-cyclobutyl-6-difluoromethoxy-2-tributylstannanyl-1H-indole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. additionAfter complete addition the bath
  2. customwas removed
  3. customTHF was then removed under vacuum
  4. filtrationthe residue filtered through silica gel
  5. concentrationthe mixture concentrated
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes