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Triethylamine → [3-(5-biphenyl-4-yl-6-fluoro-1H-benzoimidazol-2-yloxy)-phenyl]-phosphonic acid diisopropyl ester

HRID 1960136
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1960136
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:23]([F:24])=[CH:22][C:10]3[NH:11][C:12]([O:14][C:15]4[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=4)=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.C([SiH](CC)CC)C.[CH:45]([O:48][P:49]([O-:54])[O:50][CH:51]([CH3:53])[CH3:52])([CH3:47])[CH3:46]>C1(C)C=CC=CC=1.CN(C=O)C.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:45]([O:48][P:49]([C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][C:12]2[NH:11][C:10]3[CH:22]=[C:23]([F:24])[C:7]([C:4]4[CH:5]=[CH:6][C:1]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)=[CH:2][CH:3]=4)=[CH:8][C:9]=3[N:13]=2)[CH:16]=1)(=[O:54])[O:50][CH:51]([CH3:53])[CH3:52])([CH3:47])[CH3:46]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 12052TriethylsilaneHCID 21884976Phosphorous acid, bis(1-methylethyl) esterHCID 674463835-Biphenyl-4-yl-2-(3-bromo-phenoxy)-6-fluoro-1H-benzoimidazole

Produkt 1

HCID 86658719[3-(5-biphenyl-4-yl-6-fluoro-1H-benzoimidazol-2-yloxy)-phenyl]-phosphonic acid diisopropyl ester

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a microwave reactor vial was added compound 13-7 (107 mg, 0.23 mmol), PdCl2(dppf) (34 mg, 0.047 mmol), triethylamine (0.1 mL, 0.69 mmol), triethylsilane (15 μL, 0.092 mmol), diisopropylphosphite (46 μL, 0.28 mmol) in 3 mL of toluene and 0.5 mL of DMF. The reaction was run in a microwave reactor for 7 min at 140° C. The reaction mixture was diluted with EtOAc (50 mL) and washed three times with 50 mL portions of saturated aqueous ammonium chloride. The combined organic layers were dried over MgSO4 filtered and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (eluting with EtOAc/Hexanes=4/1) to yield title compound 13-8 as a brown oil.

Aufarbeitung

  1. washwashed three times with 50 mL portions of saturated aqueous ammonium chloride
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by silica gel column chromatography (eluting with EtOAc/Hexanes=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-4115b0955075453c8e912a2df20138a1
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08410284B2

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