Triethylamine → 2-Phenoxymethyl-1H-indole-5-carboxylic acid methyl ester

HRID 131247

Reaction equation

HRID 131247 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6](I)[CH:5]=1.[C:13]1([O:19][CH2:20][C:21]#[CH:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:8][CH:9]=1)[NH:10][C:21]([CH2:20][O:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:22]2)=[O:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83613(Prop-2-ynyloxy)benzeneHCID 4104649Methyl 4-amino-3-iodobenzoate

Product 1

HCID 597322132-Phenoxymethyl-1H-indole-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Resin bound 4-amino-3-iodo-benzoic acid methyl ester was suspended in DMF and treated with 15.6 g of phenyl propargylether, 60 ml of triethylamine and catalytic amounts of Cul and bis(triphenylphosphine)palladium(II) chloride. The resin was shaken for 6 h at 50° C. and washed subsequently with DMF, isopropanol/water and diethylether.

Workup

  1. washwashed subsequently with DMF, isopropanol/water and diethylether

Sources & evidence

ORD record
ord-9e1a959e9e6c4903be1e469a1db4be79
Source dataset
uspto-grants-2008_06
Patent number
US07384945B2

Linked notes

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