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Cesium carbonate → 3-[4-(2-Dimethylamino-ethoxy)-2-isopropoxy-phenylamino]-phthalic acid dimethyl ester

HRID 448382
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 448382
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10](I)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[CH3:16][N:17]([CH3:32])[CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[C:23]([O:28][CH:29]([CH3:31])[CH3:30])[CH:22]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([NH:27][C:24]2[CH:25]=[CH:26][C:21]([O:20][CH2:19][CH2:18][N:17]([CH3:32])[CH3:16])=[CH:22][C:23]=2[O:28][CH:29]([CH3:31])[CH3:30])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2326127Dimethyl 3-iodophthalateHCID 583071884-(2-Dimethylaminoethoxy)-2-isopropoxyphenylamine

Produkt 1

HCID 583073113-[4-(2-Dimethylamino-ethoxy)-2-isopropoxy-phenylamino]-phthalic acid dimethyl esterAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-iodophthalic acid dimethyl ester (2.0 g, 6.2 mmol), 4-(2-dimethylaminoethoxy)-2-isopropoxyphenylamine (1.5 g, 6.2 mmol), Pd2(dba)3 (0.26 g, 0.28 mmol), rac-BINAP (0.12 g, 0.19 mmol), and cesium carbonate (2.8 g, 8.6 mmol), in 12 mL toluene was heated to reflux under nitrogen for 24 hours. The reaction mixture was cooled, diluted with CH2Cl2 (20 mL), and filtered through Celite, and the filter was washed with additional CH2Cl2 (60 mL). The filtrate was evaporated in vacuo, and the residue was purified by ISCO silica gel flash chromatography using a methylene chloride-methanol gradient, eluting 1.3 g of the product at 96:4 methylene chloride-methanol, in 47% yield; 1H NMR (CDCl3) δ 1.31 (d, J=6.1 Hz, 6H), 2.96 (d, J=4.8 Hz, 6H), 3.41-3.47 (m, 2H), 3.87 (s, 6H), 4.47-4.51 (m, 3H), 6.45 (dd, J=8.7 Hz, J=2.6 Hz, 1H), 6.56 (d, J=2.6 Hz, 1H), 7.07 (dd, J=6.0 Hz, J=2.5 Hz, 1H), 7.18 (d, J=8.7 Hz, 1H), 7.20-7.18 (m, 2H), 7.90 (s, 1H).

Aufarbeitung

  1. temperatureto reflux under nitrogen for 24 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through Celite
  4. washthe filter was washed with additional CH2Cl2 (60 mL)
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by ISCO silica gel flash chromatography
  7. washeluting 1.3 g of the product at 96:4 methylene chloride-methanol

Quellen und Nachweise

ORD-Eintrag
ord-f0485f090fdb41a5b6e4126d0d0ae622
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08481568B2

Notizen zur Reaktion

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