Diisopropylethylamine → tert-Butyl {3-[(3-aminophenyl)ethynyl]phenyl}carbamate

HRID 541732Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])#[CH:2].I[C:11]1[CH:12]=[C:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:14]=[CH:15][CH:16]=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>[NH2:6][C:5]1[CH:4]=[C:3]([C:1]#[C:2][C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH:14]=[CH:15][CH:16]=2)[CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-ethynylaniline (1.16 g, 9.87 mmol) and tert-butyl (3-iodophenyl)carbamate (3.0 g, 9.4 mmol) in THF (28 mL) was treated with bis(triphenylphosphine)palladium(II) chloride (330 mg, 0.47 mmol), copper(I) iodide (140 mg, 0.75 mmol) and N,N-diisopropylethylamine (3.27 ml, 18.8 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 (1.42 g, 49%). LCMS for C19H21N2O2 (M+H)+: m/z=309.1.

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-50640c9103914e10afc7c4d77d7d38b8
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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