Lithium Hexamethyldisilazide → 7-Isopropenyl-5-aminoindole

HRID 380604Notes

Reaction equation

HRID 380604 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[Li+].[NH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[C:19]([C:21](=O)[CH3:22])[CH:20]=1)[NH:17][CH:16]=[CH:15]2>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:21]([C:19]1[CH:20]=[C:12]([NH2:11])[CH:13]=[C:14]2[C:18]=1[NH:17][CH:16]=[CH:15]2)([CH3:22])=[CH2:1]

Participants

5

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 154534695-Amino-7-acetylindole

Product 1

HCID 227280387-Isopropenyl-5-aminoindoleYield 83.9%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of methyltriphenylphosponium bromide (3.8 g, 10 mmol) in 40 mL of THF was added 15 mL of a solution of lithium bis(trimethylsilyl)amide (15 mmol) and the resulting reaction mixture was stirred for 1 h at −78° C. A solution of 5-amino-7-acetylindole (0.55 g, 3.1 mmol) in 10 mL of THF was added into the solution slowly for 0.5 h period. The reaction mixture was slowly warmed to 25° C. and stirred for 12 h at the temperature. Column chromatographic separation of reaction mixture (50% EtOAc/n-Hexane) provided 0.45 g (2.6 mmol, 82%) of the desired product.

Workup

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture was slowly warmed to 25° C.
  3. stirringstirred for 12 h at the temperature
  4. customColumn chromatographic separation of reaction mixture (50% EtOAc/n-Hexane)

Sources & evidence

ORD record
ord-3140b0f8ba474d41a923a871a11a8ed3
Source dataset
uspto-grants-2001_10
Patent number
US06303643B1

Reaction notes

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