Ethyl3-Amino-4-(3-methylbut-1-ynyl)benzoate → Ethyl2-Isopropyl-1H-indole-6-carboxylate

HRID 40059Notes

Reaction equation

HRID 40059 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][CH:13]([CH3:15])[CH3:14])=[C:7]([NH2:16])[CH:6]=1)[CH3:2]>CN(C=O)C.[Cu]I>[CH:13]([C:12]1[NH:16][C:7]2[C:8]([CH:11]=1)=[CH:9][CH:10]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:17])[CH:6]=2)([CH3:14])[CH3:15]

Participants

4

Reactant 1

HCID 59762350Ethyl3-Amino-4-(3-methylbut-1-ynyl)benzoate2×

Product 1

HCID 59762345Ethyl2-Isopropyl-1H-indole-6-carboxylate

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 ethyl3-amino-4-(3-methylbut-1-ynyl)benzoate (Compound 32, 5.30 g, 22.9 mmol) in DMF (50 ml) at 25° C. under argon then added CuI (218 mg, 11.5 mmol). The reaction was heated for 2 h at 160° C., filtered off black solid, and then rinsed solid with EtOAc, organic layer was concentrated in vacuo. The residue was purified by chromatography on silica gel (0→20% EtOAc-hexanes) to yield the title compound as a yellow solid.

Workup

  1. customat 25° C.
  2. filtrationfiltered off black solid
  3. washrinsed solid with EtOAc, organic layer
  4. concentrationwas concentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (0→20% EtOAc-hexanes)

Sources & evidence

ORD record
ord-51f34c0cc11647aca3b767c4dce384dd
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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