Triethylsilane → 4-Chloroindoline

HRID 544915Notes

Reaction equation

HRID 544915 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:6]2

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 913454-Chloroindole

Product 1

HCID 30163064-ChloroindolineYield 90.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-chloroindole (3.15 g) and triethylsilane (8.30 ml) in trifluoroacetic acid (32 ml) was stirred at 50° C. for 30 minutes. The solvent was evaporated under reduced pressure, and the residue was basified with a saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate twice, and the combined organic layer was dried over magnesium sulfate. The insoluble materials were filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-80:20) to give the titled compound (2.89 g) as colorless oil. APCI-Mass m/Z 154/156 (M+H). 1H-NMR (DMSO-d6) δ 2.94 (t, J=8.7 Hz, 2H), 3.46 (t, J=8.7 Hz, 2H), 5.83 (s, 1H), 6.40 (d, J=7.7 Hz, 1H), 6.50 (d, J=8.0 Hz, 1H), 6.90 (t, J=7.9 Hz, 1H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionThe mixture was extracted with ethyl acetate twice
  3. dry with materialthe combined organic layer was dried over magnesium sulfate
  4. filtrationThe insoluble materials were filtered off
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-80:20)

Sources & evidence

ORD record
ord-7f7bc41dae8a4570a930edacd3540cd5
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

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