6-Nitro-1H-indole → HCID 66842111, compound

HRID 1158831Notes

Reaction equation

HRID 1158831 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([Li])CCC.Cl[Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21]>O1CCCC1>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 785026-Nitro-1H-indoleHCID 139400Triisopropylsilyl chlorideHCID 178418339Butyllithium

Product 1

HCID 66842111HCID 66842111, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

i)—A solution of 6-nitroindole (25 g, 154 mmol) in dry tetrahydrofuran (900 ml) was cooled to −78° C. and treated with n-butyllithium (2.5 M solution in hexanes, 67.0 ml, 169 mmol). After 20 min. stirring, chloro-triisopropyl-silane (33.0 ml, 155 mmol) was added. The cooling bath was removed and the reaction mixture was stirred for 2 h. The mixture was quenched with water and the product was extracted into ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (heptane/ethyl acetate 95:5) afforded 6-nitro-1-triisopropylsilanyl-1H-indole (41.5 g).

Workup

  1. customThe cooling bath was removed
  2. stirringthe reaction mixture was stirred for 2 h
  3. customThe mixture was quenched with water
  4. extractionthe product was extracted into ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b1d485ee47c64d6396416ceda9b89af4
Source dataset
uspto-grants-2010_10
Patent number
US07812036B2

Reaction notes

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