Trifluoroacetic acid → 2-Ethyl-6-methoxy-1H-indole

HRID 985277Notes

Reaction equation

HRID 985277 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17](=O)[CH2:18][CH3:19])(C)(C)C.C(O)(C(F)(F)F)=O>C1COCC1>[CH2:18]([C:17]1[NH:7][C:8]2[C:9]([CH:16]=1)=[CH:10][CH:11]=[C:12]([O:14][CH3:15])[CH:13]=2)[CH3:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20767945[5-Methoxy-2-(2-oxo-butyl)-phenyl]-carbamic acid t-butyl Ester

Product 1

HCID 221436442-Ethyl-6-methoxy-1H-indoleYield 166.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [5-methoxy-2-(2-oxo-butyl)-phenyl]-carbamic acid t-butyl ester 73b (1.36 g, 4.65 mmole) in 10 ml THF was added 4 ml TFA. The reaction mixture was stirred at room temperature for 5 h, quenched with 50 ml H2O and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The residue was purified by flash column chromatography (10-15% EtOAc in hexane) to give pale yellow solid (1.36 g, 73%). 1H NMR (CDCl3) δ7.75 (1H, bs), 7.49 (1H, d, J=8.6 Hz), 6.81 (1H, s), 6.73 (1H, d, J=8.6 Hz), 3.83 (3H, s), 2.75 (2H, q, J=7.5 Hz), 1.32 (3H, t, J=7.5 Hz). ESIMS (MH+): 272.10.

Workup

  1. customquenched with 50 ml H2O
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (10-15% EtOAc in hexane)

Sources & evidence

ORD record
ord-6d1a83d49e094c669177e58c8f238d96
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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