Triphenylphosphine → methyl 2-(2,6-dimethylphenyl)-1H-indole-6-carboxylate

HRID 1514930Notes

Reaction equation

HRID 1514930 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]#[C:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=1[NH:21]C(=O)C(F)(F)F.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[NH:21][C:12]2[C:11]([CH:10]=1)=[CH:20][CH:19]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 86651266Methyl 4-(2,6-dimethylphenylethynyl)-3-(2,2,2-trifluoroacetylamino)-benzoate

Product 1

HCID 66966102methyl 2-(2,6-dimethylphenyl)-1H-indole-6-carboxylate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of methyl 4-(2,6-dimethylphenylethynyl)-3-(2,2,2-trifluoroacetylamino)-benzoate (103 mg, 270 μmol), copper (I) iodide (2 mg, 10 μmol), triphenylphosphine (6 mg, 23 μmol), and K3PO4 (117 mg, 550 μmol) in dioxane (2 mL) was heated at 115° C. in a microwave apparatus for 15 min. The solution was concentrated, then chromatographed using a gradient of 0-40% heptane/ethyl acetate to afford methyl 2-(2,6-dimethylphenyl)-1H-indole-6-carboxylate.

Workup

  1. concentrationThe solution was concentrated
  2. customchromatographed

Sources & evidence

ORD record
ord-be20f2bccbf9495ba20d5cf6beefd489
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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