Triethylamine → HCID 53700466, compound

HRID 1608931Notes

Reaction equation

HRID 1608931 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:20](O)=[O:21])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.ClC(OCC)=O.[CH2:36]([NH:38][CH:39]([CH3:41])[CH3:40])[CH3:37]>O1CCCC1>[CH2:36]([N:38]([CH:39]([CH3:41])[CH3:40])[C:20]([C:12]1[N:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:19]2[C:14]([CH:13]=1)=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:21])[CH3:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 88318IsopropylethylamineHCID 20083234HCID 20083234, compound

Product 1

HCID 53700466HCID 53700466, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

1-(3,4-Dimethoxyphenyl)indole-2-carboxylic acid (2.0 g, 6.8 mmol) was stirred in tetrahydrofuran (10 ml). Triethylamine (1 ml, 7.5 mmol) was added and the mixture was cooled to 0° C. Ethyl chloroformate (0.7 ml, 7 mmol) was added dropwise, followed by stirring for 30 minutes. N-ethyl isopropylamine (0.6 g, 7 mmol) in tetrahydrofuran was added, followed by stirring for 30 minutes and refluxing for 6 hours. The tetrahydrofuran was evaporated in vacuo, and the residue was dissolved in toluene. The toluene solution was washed with water, dried, evaporated in vacuo, applied onto a flash chromatography column (silica gel, 30 g) and eluted with toluene/acetone (9.5:0.5). The desired fractions were concentrated and the residue triturated with diisopropyl ether to give 1-(3,4-dimethoxyphenyl)indole-2-carboxylic acid N-ethyl isopropyl amide as white crystals which were then filtered and dried. Yield: 50 mg (2% of theoretical). Rf : 0.53 (toluene/acetone 7:3). The H-NMR spectra was consistent with the assigned structure.

Workup

  1. stirringby stirring for 30 minutes
  2. temperaturerefluxing for 6 hours
  3. customThe tetrahydrofuran was evaporated in vacuo
  4. dissolutionthe residue was dissolved in toluene
  5. washThe toluene solution was washed with water
  6. customdried
  7. customevaporated in vacuo
  8. washeluted with toluene/acetone (9.5:0.5)
  9. concentrationThe desired fractions were concentrated
  10. customthe residue triturated with diisopropyl ether

Sources & evidence

ORD record
ord-1b37044db20042abaff51f776f2565d9
Source dataset
uspto-grants-1995_03
Patent number
US05399559

Reaction notes

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