Trimethyltin chloride → HCID 18177246, compound

HRID 394596Notes

Reaction equation

HRID 394596 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[Li]CCCC.[CH3:23][Sn:24](Cl)([CH3:26])[CH3:25]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([Sn:24]([CH3:26])([CH3:25])[CH3:23])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 15006438HCID 15006438, compoundHCID 178418339Butyllithium

Product 1

HCID 18177246HCID 18177246, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

1-(4-Fluorophenyl)-5-bromo-1H-indole (5 g, 17.2 mmol) in THF (20 mL) was added during 3 minutes to a solution of n-BuLi (1.6 M, 26 mmol) in THF (200 mL) at −78° C. The solution was stirred for 4 minutes at −78° C. before addition of trimethylstannyl chloride (10 g, 50 mmol) in THF (10 mL). The reaction mixture was allowed to warn up to room temperature and stirred for 1 h. After evaporation of the solvent the crude product was purified by flash chromatography (EtOAc/Heptane 5/100). Yield: 3.6 g. Mp 61-63° C. (EtOAc/Heptane).

Workup

  1. customto warn up to room temperature
  2. customAfter evaporation of the solvent the crude product
  3. customwas purified by flash chromatography (EtOAc/Heptane 5/100)

Sources & evidence

ORD record
ord-331bfcafa42040c7b1594fefc6e70016
Source dataset
uspto-grants-2003_08
Patent number
US06602889B1

Reaction notes

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