Triphenylphosphine → Methyl 2-(2-(3-phenyl-7-propylbenzofuran-6-yloxy)-ethyl)-indole-5-acetate

HRID 2288872Notes

Reaction equation

HRID 2288872 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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:37]1([C:43]2[C:47]3[CH:48]=[CH:49][C:50](O)=[C:51]([CH2:52][CH2:53][CH3:54])[C:46]=3[O:45][CH:44]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:37]1([C:43]2[C:47]3[CH:48]=[CH:49][C:50]([O:1][CH2:2][CH2:3][C:4]4[NH:5][C:6]5[C:11]([CH:12]=4)=[CH:10][C:9]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=5)=[C:51]([CH2:52][CH2:53][CH3:54])[C:46]=3[O:45][CH:44]=2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 15462903Methyl 2-(2-hvdroxyethyl)indole-5-acetateHCID 154629143-Phenyl-7-propyl-1-benzofuran-6-ol

Product 1

HCID 15462901Methyl 2-(2-(3-phenyl-7-propylbenzofuran-6-yloxy)-ethyl)-indole-5-acetateYield 24.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the methyl 2-(2-hydroxyethyl)indole-5-acetate (37.6 mg; 0.16 mmol), Ph3P (47 mg; 1.1 eq), 3-phenyl-6-hydroxy-7-propylbenzofuran (45 mg; 1.1 eq) and THF (5 mL) was added diisopropyl azodicarboxylate (35 ,uL; 1.1 eq), and the mixture was stirred at room temperature overnight. The mixture was concentrated and chromatographed (silica gel, hexane:ethyl acetate::9:1 to 4:1) affording 18.6 mg of the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customchromatographed (silica gel, hexane:ethyl acetate::9:1 to 4:1)

Sources & evidence

ORD record
ord-90aa7aea2e0048a6b732b0c2884d0139
Source dataset
uspto-grants-2000_07
Patent number
US06090839

Reaction notes

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