HCID 12628585, compound → Ethyl 3-methyl-1H-indole-5-carboxylate

HRID 2085550Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[CH:8][C:3]=1[NH:4][CH2:5][CH:6]=[CH2:7]>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:12]([C:10]1[CH:11]=[C:2]2[C:3](=[CH:8][CH:9]=1)[NH:4][CH:5]=[C:6]2[CH3:7])([O:14][CH2:15][CH3:16])=[O:13]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-bromo-4-carboethoxy-N-allylaniline (J. Org. Chem., 45, 2710(1980)) (650 mg, 2.29 mmol) in acetonitrile (10 ml), tetrakis(triphenylphosphine)palladium(0) (132 mg, 0.114 mmol), palladium (II) acetate (25.7 mg, 0.114 mmol) and TEA (0.413 ml, 2.98 mmol) were added and stirred overnight in a sealed tube at 100° C. After filtering the reaction mixture, the filtrate was evaporated under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:2) to give the titled compound (340 mg, 73%).

Workup

filtrationAfter filtering the reaction mixture
customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-9f18917448df481b93bfa5a8b3971278
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06720433B2

Reaction notes

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