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Sodium Carbonate → HCID 59738189, Verbindung

HRID 561238
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 561238
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:29])=[C:6]([CH:28]=1)[O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:18]=[C:17]([C:19]3[N:20]=[N:21][N:22]([CH2:24][C:25]([OH:27])=[O:26])[N:23]=3)[O:16][N:15]=2)[CH2:10][CH2:9]1.[F:30][C:31]([F:43])([F:42])[O:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:29][C:5]1[CH:4]=[CH:3][C:2]([C:36]2[CH:35]=[CH:34][C:33]([O:32][C:31]([F:30])([F:42])[F:43])=[CH:38][CH:37]=2)=[CH:28][C:6]=1[O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:18]=[C:17]([C:19]3[N:20]=[N:21][N:22]([CH2:24][C:25]([OH:27])=[O:26])[N:23]=3)[O:16][N:15]=2)[CH2:10][CH2:9]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 24988884HCID 24988884, Verbindung

Produkt 1

HCID 59738189HCID 59738189, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of (5-{3-[4-(5-bromo-2-chlorophenoxy)piperidin-1-yl]isoxazol-5-yl}-2H-tetrazol-2-yl)acetic acid (130 mg, 0.269 mmol), [4-(trifluoromethoxy)phenyl]boronic acid (98 mg, 0.476 mmol) and Pd(Ph3P)4 (25 mg, 0.022 mmol) in toluene (4 mL) was added aqueous 2 M Na2CO3 (1.5 mL, 3.00 mmol). After the resulting heterogeneous mixture was purged with nitrogen, it was gently heated to 80° C. for 6 h with stirring under a nitrogen atmosphere. After cooling to room temperature, the reaction was poured into aqueous 1 N HCl and extracted with EtOAc. The organic layer was washed with brine and dried (Na2SO4). Solvents were removed under reduced pressure and the crude material was purified by column chromatography on silica gel (gradient from 0% to 3% HOAc/EtOAc). After concentration, the white solid was co-evaporated twice and triturated with Et2O/heptane to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ13.92 (br s, 1H), 7.88-7.83 (m, 2H), 7.57-7.54 (m, 2H), 7.49 (d, 2H), 7.30 (dd, 1H), 7.27 (s, 1H), 5.83 (s, 2H), 5.00-4.93 (m, 1H), 3.68-3.60 (m, 2H), 3.41-3.35 (m, 2H), 2.12-2.02 (s, 2H), 1.87-1.78 (m, 2H). MS: m/z 565 (MH+).

Aufarbeitung

  1. customAfter the resulting heterogeneous mixture was purged with nitrogen, it
  2. temperatureAfter cooling to room temperature
  3. additionthe reaction was poured into aqueous 1 N HCl
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customSolvents were removed under reduced pressure
  8. customthe crude material was purified by column chromatography on silica gel (gradient from 0% to 3% HOAc/EtOAc)
  9. concentrationAfter concentration
  10. customtriturated with Et2O/heptane

Quellen und Nachweise

ORD-Eintrag
ord-2f22af56542a47fe9855fa79c585b553
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08063224B2

Notizen zur Reaktion

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