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

HRID 3382Notes

Reaction equation

HRID 3382 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-a1ba7dd968ef42de8f7d8852721b5d4d
Source dataset
uspto-grants-1998_03
Patent number
US05733923

Reaction notes

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