Diisopropylethylamine → N-{2-[4-(2-Cyclopentyloxy-pyrimidin-5-ylethynyl)-phenyl]-1-methyl-ethyl}-acetamide

HRID 76204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 76204
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=1)#[CH:2].Br[C:17]1[CH:18]=[N:19][C:20]([O:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[N:21][CH:22]=1.CCN(C(C)C)C(C)C>C1COCC1.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>[CH:24]1([O:23][C:20]2[N:19]=[CH:18][C:17]([C:2]#[C:1][C:3]3[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=3)=[CH:22][N:21]=2)[CH2:25][CH2:26][CH2:27][CH2:28]1

Komponenten

7

Edukt 3

HCID 81531DiisopropylethylamineHCID 497587165-Bromo-2-cyclopentyloxypyrimidineHCID 86669621N-(1-(4-ethynylphenyl)propan-2-yl)acetamide

Produkt 1

HCID 56925027N-{2-[4-(2-Cyclopentyloxy-pyrimidin-5-ylethynyl)-phenyl]-1-methyl-ethyl}-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 33.1 mg (0.17 mmol) N-[2-(4-ethynyl-phenyl)-1-methyl-ethyl]-acetamide (I58.3) and 40.0 mg (0.17 mmol) 5-bromo-2-cyclopentyloxypyrimidine (I14.1) in 2.0 mL THF are added 11.6 mg (0.02 mmol) bis(triphenylphosphin)palladiumdichlorid, 1.57 mg (8.00 μmol) CuI and 56.0 μL (0.33 mmol) DIPEA. The reaction mixture is stirred at r.t. over night. The solvent is removed in vacuo and the residue is purified by HPLC (MeOH/H2O/TFA).

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by HPLC (MeOH/H2O/TFA)

Quellen und Nachweise

ORD-Eintrag
ord-082f8a11a6c54529a16876e06bae65c3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835472B2

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