5-Methoxy-2-(3-methylbut-1-ynyl)aniline → 2-Isopropyl-6-methoxy-1H-indole

HRID 40132Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of 5-methoxy-2-(3-methylbut-1-ynyl)aniline (Compound 135, 1.8 g, 9.5 mmol) in DMF (20 ml) was added CuI (101 mg, 0.53 mmol). The reaction was stirred at 160° C. for 1.5 h. The solvent was removed in vacuo and the residue was purified by chromatography on silica gel (0→25% EtOAc-hexanes) to yield the title compound as a brownish red solid.

Workup

customThe solvent was removed in vacuo
customthe residue was purified by chromatography on silica gel (0→25% EtOAc-hexanes)

Sources & evidence

ORD record: ord-d729692a87884250a6619b9f8339b84e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524917B2

Reaction notes

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