HCID 66658583, compound → 2-Isopropyl-1H-indole

HRID 420815Notes

Reaction equation

HRID 420815 reaction equation
[CH3:1][CH:2]([CH3:12])[C:3]#[C:4][C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7]>CN(C=O)C.[Cu]I>[CH:2]([C:3]1[NH:7][C:6]2[C:5]([CH:4]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([CH3:12])[CH3:1]

Participants

4

Reactant 1

HCID 66658583HCID 66658583, compound2×

Product 1

HCID 873072-Isopropyl-1H-indole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 2-(3-methylbut-1-ynyl)aniline (Compound 37, 3.47 g, 21.8 mmol) in DMF (100 ml) was added copper (I) iodide (41 mg, 0.22 mmol). The mixture was stirred at 160° C. for 2 h and was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with 5% EtOAc-hexanes to yield 2-isopropyl-1H-indole (Compound 38) as an off-white solid.

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel eluting with 5% EtOAc-hexanes

Sources & evidence

ORD record
ord-992fd5af865b4605ba207428b6255660
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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