Diisopropylethylamine → Methyl 3-({3-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)-5-nitrobenzoate

HRID 541739Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])#[CH:2].I[C:17]1[CH:18]=[C:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=[CH:21][CH:22]=1.C(N(CC)C(C)C)(C)C>C1COCC1.O.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.[Cu]I>[C:26]([O:25][C:24]([NH:23][C:19]1[CH:18]=[C:17]([C:2]#[C:1][C:3]2[CH:4]=[C:5]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=2)[C:6]([O:8][CH3:9])=[O:7])[CH:22]=[CH:21][CH:20]=1)=[O:30])([CH3:29])([CH3:27])[CH3:28]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of methyl 3-ethynyl-5-nitrobenzoate (1.45 g, 7.08 mmol), tert-butyl (3-iodophenyl)carbamate (2.26 g, 7.08 mmol) in THF (28 mL) was treated with bis(triphenylphosphine)palladium(II) chloride (248 mg, 0.354 mmol), copper(I) iodide (108 mg, 0.566 mmol) and N,N-diisopropylethylamine (2.47 mL, 14.2 mmol) and stirred at 25° C. overnight. The reaction was diluted with water and extracted with ethyl acetate three times. The combined organic solutions were dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (1.85 g, 66%). LCMS for C21H20N2O6Na (M+Na)+: m/z=419.3.

Workup

extractionextracted with ethyl acetate three times
dry with materialThe combined organic solutions were dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-3fd59af59e0740c88504cfa6e3248095
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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