1-(2-(Tert-butoxycarbonylamino)-5-methoxyphenyl]-2-butanone → 2-ethyl-5-methoxy-1H-indole

HRID 581441Notes

Reaction equation

HRID 581441 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[CH2:17][C:18](=O)[CH2:19][CH3:20])=O)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[CH2:19]([C:18]1[NH:8][C:9]2[C:10]([CH:17]=1)=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[CH3:20]

Participants

4

Reactant 1

HCID 105178251-(2-(Tert-butoxycarbonylamino)-5-methoxyphenyl]-2-butanone

Product 1

HCID 107024052-ethyl-5-methoxy-1H-indoleYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1-[2-(tert-Butoxycarbonylamino)-5-methoxyphenyl]-2-butanone (7.33 g, 0.025 mol) in 120 mL of CH2Cl2 and 20 mL of trifluoroacetic acid was stirred for 20 hours, washed with water, NaHCO3 solution and the product chromatographed on silica (eluted with 20% EtOAc/hexane) to give 2.54 g (58% yield) of 2-ethyl-5-methoxy-1H-indole as a white solid, mp 49-50° C.

Workup

  1. washwashed with water, NaHCO3 solution
  2. customthe product chromatographed on silica (eluted with 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-fa610833136940968d62b1dcfe585d68
Source dataset
uspto-grants-1999_07
Patent number
US05919943

Reaction notes

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