Indole → HCID 15677792, compound

HRID 1275122Notes

Reaction equation

HRID 1275122 reaction equation
OCCC1N[C:6]2[C:11](C=1)=[CH:10][C:9](CC(OC)=O)=[CH:8][CH:7]=2.[O:18]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27](CCC)[CH:26]=1)[C:19]1C=CC=[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>[CH2:19]([O:18][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH:27][CH:26]=1)[CH:20]=[CH2:21]

Participants

7

Reactant 5

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

Product 1

HCID 15677792HCID 15677792, compoundYield 122.1%

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-c426fb1f7cf5410896178034f1bf8e42
Source dataset
uspto-grants-2000_12
Patent number
US06160000

Reaction notes

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