tert-Butoxy bis(dimethylamino)methane → 5-Isopropoxy-1H-indole

HRID 1017590Notes

Reaction equation

HRID 1017590 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[C:7]([CH3:14])[CH:6]=1)([CH3:3])[CH3:2].[C:15](OC(N(C)C)N(C)C)(C)(C)C>>[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[C:8](=[CH:9][CH:10]=1)[NH:11][CH:15]=[CH:14]2)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 184035344-Isopropoxy-2-methyl-1-nitrobenzene

Product 1

HCID 167380545-Isopropoxy-1H-indoleYield 96%

Procedure

A mixture of 4-isopropoxy-2-methyl-1-nitrobenzene (3.55 g,0.018 mol) and tert-butoxybis(dimethylamino)methane (9 mL) was refluxed for 4 hours and the volatile was removed. The dark brown residue was dissolved in THF (150 mL) and hydrogenated with catalytic amount of 10% Pd on Carbon with H2 in a balloon. After stirring at room temperature overnight, the catalyst was filtered off and the filtrate was concentrated to afford 3.07 g 5-isopropoxyindole (96%). MS(EI): (M+1) 176.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customthe volatile was removed
  3. dissolutionThe dark brown residue was dissolved in THF (150 mL) and hydrogenated with catalytic amount of 10% Pd on Carbon with H2 in a balloon
  4. filtrationthe catalyst was filtered off
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-418f9d4d11774b9a9b59568312a7bfb1
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

Loading…