Indole → 2-(2-(4-Phenoxy-2-propylphenoxy)ethyl)indole-5-acetic acid methyl ester

HRID 1057803Notes

Reaction equation

HRID 1057803 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=2.[O:18]([C:25]1[CH:30]=[CH:29][C:28](O)=[C:27]([CH2:32][CH2:33][CH3:34])[CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.N1C2C(=CC=CC=2)C=C1>C1COCC1>[CH3:17][O:16][C:14](=[O:15])[CH2:13][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4]([CH2:3][CH2:2][O:1][C:28]1[CH:29]=[CH:30][C:25]([O:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:26][C:27]=1[CH2:32][CH2:33][CH3:34])=[CH:12]2

Participants

7

Reactant 5

HCID 798IndoleHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 15462903Methyl 2-(2-hvdroxyethyl)indole-5-acetateHCID 154629044-Phenoxy-2-propylphenol

Product 1

HCID 154629052-(2-(4-Phenoxy-2-propylphenoxy)ethyl)indole-5-acetic acid methyl esterYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(2-hydroxyethyl)indole-5-acetate from Example 1, Step E (7.6 g), 4-phenoxy-2-propylphenol (8.28 g), triphenylphosphine (11.2 g), DIAD (8.5 mL) and THF (125 mL) was stirred under nitrogen at room temperature. After stirring overnight none of the starting indole remained as determined by TLC and the reaction was concentrated to a yellow oil. The oil was purified by silca gel chromatography (10%-20% ethyl acetate in hexanes) to give the desired product (9.0 g).

Workup

  1. concentrationthe reaction was concentrated to a yellow oil
  2. customThe oil was purified by silca gel chromatography (10%-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f30cc2c60a034fa9ae76790f6c74fb6c
Source dataset
uspto-grants-2003_02
Patent number
US06515015B1

Reaction notes

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