HCID 117700269, compound → Methyl 6-ethyl-1H-indole-2-carboxylate

HRID 589619Notes

Reaction equation

HRID 589619 reaction equation
[N:1]([C:4](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])=[N+]=[N-]>CC1C=CC(C)=CC=1>[CH2:16]([C:13]1[CH:14]=[C:15]2[C:10]([CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[NH:1]2)=[CH:11][CH:12]=1)[CH3:17]

Participants

3

Reactant 1

HCID 117700269HCID 117700269, compound

Product 1

HCID 4715300Methyl 6-ethyl-1H-indole-2-carboxylateYield 59.1%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

Methyl 2-azido-3-(4-ethylphenyl)acrylate (36) (1.0 g, 4.33 mmol) was dissolved in p-xylene and heated at reflux for 3 h. After evaporation of the solvent, the residue was purified by flash column chromatography eluting with a linear gradient ranging from 0 to 20% EtOAc-hexanes to provide 0.52 g (59%) of product 37 as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 1.28 (t, J=7 Hz, 3H), 2.79 (q, J=7 Hz, 2H), 3.94 (s, 3H), 7.03 (dd, J=2, 8 Hz, 1H), 7.17-7.18 (m, 1H), 7.21-7.23 (m, 1H), 7.60 (d, J=8 Hz, 1H), 8.78 (s, 1H). LC-MS (CI): m/z 202.0 [(M−H)− C12H13NO2 requires 203.09].

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by flash column chromatography
  5. washeluting with a linear gradient

Sources & evidence

ORD record
ord-017316d656c740afa26875933969a444
Source dataset
uspto-grants-2016_01
Patent number
US09233921B2

Reaction notes

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