Tripropylamine → 1H-Indole-5-acetic acid, 3-(ethoxycarbonyl)-2-methyl-, ethyl ester

HRID 2301326Notes

Reaction equation

HRID 2301326 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH:5]=[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][C:10]=1I)[CH3:7])[CH3:2].C(N(CCC)CCC)CC.C(OCC)(=O)C>CN(C=O)C>[CH2:1]([O:3][C:4]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:13]=2)[NH:8][C:6]=1[CH3:7])=[O:22])[CH3:2]

Participants

5

Reactant 3

HCID 7616TripropylamineHCID 8857Ethyl AcetateHCID 701032823-(4-Ethoxycarbonylmethyl-2-iodo-phenylamino)but-2-enoic acid ethyl ester

Product 1

HCID 113237171H-Indole-5-acetic acid, 3-(ethoxycarbonyl)-2-methyl-, ethyl esterYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-(4-ethoxycarbonylmethyl-2-iodo-phenylamino)but-2-enoic acid ethyl ester (12.5 g, 30 mmol) in DMF (30 mL), tripropylamine (4.3 g, 30 mmol), and Pd(II)acetate (0.33 g, 1.5 mmol) are added, and the reaction mixture is heated at 120° C. for 1 hour. After cooling to room temperature, ethyl acetate (150 mL) is added. The organic layer is washed with water (2×100 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The crude material is recrystallized from hexane/ethyl acetate to give a yellow-orange solid (3.3 g, 38%). MS: 290 (M+1)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe organic layer is washed with water (2×100 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material is recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-3a0fee1be56f46f190e49226316ae6b5
Source dataset
uspto-grants-2002_12
Patent number
US06500837B2

Reaction notes

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