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Aniline → HCID 11611884, Verbindung

HRID 506279
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 506279
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]3[O:20][C:19]([C:21]4[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=4)=[N:18][C:17]=13)=[O:11])[CH2:2]2.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=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+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]3[O:20][C:19]([C:21]4[CH:26]=[CH:25][C:24]([NH:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:23][CH:22]=4)=[N:18][C:17]=13)=[O:11])[CH2:2]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6115AnilineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 11518485HCID 11518485, Verbindung

Produkt 1

HCID 11611884HCID 11611884, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845
palladium(II) acetate
Katalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of N-(1-azabicyclo[2.2.2]oct-3-yl)-2-(4-iodophenyl)benzoxazole-4-carboxamide (27 mg, 0.057 mmol), aniline (10.4 μL, 0.114 mmol), palladium acetate (1.3 mg, 0.0057 mmol), racemic BINAP (10.6 mg, 0.017 mmol) and toluene (2 mL) was stirred under nitrogen at room temperature for 30 min. Cesium carbonate (37 mg, 0.11 mmol) was added and the mixture was heated at 110° C. under nitrogen for 5 h. The mixture was cooled to room temperature, quenched with saturated aqueous sodium bicarbonate, extracted with methylene chloride. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The crude material was purified by semi-preparative HPLC to afford N-(1-azabicyclo[2.2.2]oct-3-yl)-2-(4-phenylaminophenyl)benzoxazole-4-carboxamide (21 mg, 84%) as a light yellow solid: 1H NMR (500 MHz, CDCl3) δ 9.66 (d, J=7.5 Hz, 1H), 8.15 (dd, J=8.0, 1.0 Hz, 1H), 8.09 (dd, J=7.5, 2.0 Hz, 2H), 7.66 (dd, J=8.0, 1.0 Hz, 1H), 7.41-7.36 (m, 3H), 7.22 (d, J=7.5 Hz, 2H), 7.12-7.10 (m, 3H), 6.15 (s, 1H), 4.32-4.28 (m, 1H), 3.52 (ddd, J=14.0, 9.5, 2.0 Hz, 1H), 3.10-2.81 (m, 5H), 2.17-2.06 (m, 2H), 1.78-1.64 (m, 3H); MS (ESI+) m/z 439 (M+H); HPLC>99% (AUC), tR=14.32 min.

Aufarbeitung

  1. temperaturethe mixture was heated at 110° C. under nitrogen for 5 h
  2. temperatureThe mixture was cooled to room temperature
  3. customquenched with saturated aqueous sodium bicarbonate
  4. extractionextracted with methylene chloride
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by semi-preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-06540a0458e5455f95dd02ff786bd901
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07781430B2

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