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Sodium Carbonate → 2-[3,5-bis(trifluoromethyl)phenyl]-N-(6'-chloro-6-fluoro-2-methyl-3,4'-bipyridin-3'-yl)-N,2-dimethylpropanamide

HRID 2245415
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2245415
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([C:13]([CH3:27])([CH3:26])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([Cl:25])=[CH:22][C:23]=2I)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[F:30][CH:31]1[CH2:36][CH2:35][CH:34](B(O)O)[CH:33]([CH3:40])[NH:32]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([C:13]([CH3:27])([CH3:26])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([Cl:25])=[CH:22][C:23]=2[C:34]2[C:33]([CH3:40])=[N:32][C:31]([F:30])=[CH:36][CH:35]=2)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 666585522-Fluoro-6-methylpiperidine-5 boronic acidHCID 866241982-[3,5-bis(trifluoromethyl)phenyl]-N-(6-chloro-4-iodo-3-pyridinyl)-N,2-dimethylpropanamide

Produkt 1

HCID 592158222-[3,5-bis(trifluoromethyl)phenyl]-N-(6'-chloro-6-fluoro-2-methyl-3,4'-bipyridin-3'-yl)-N,2-dimethylpropanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-[3,5-bis(trifluoromethyl)phenyl]-N-(6-chloro-4-iodo-3-pyridinyl)-N,2-dimethylpropanamide (200 mg, 0.363 mmol), 2-fluoro-6-methylpiperidine-5 boronic acid (73 mg, 0.472 mmol), sodium carbonate solution (0.4 mL, 2M), tetrakistriphenylphosphinepalladium (4 mg, 0.00363 mmol) in dioxan (2 mL) were heated together in the microwave at 110° C. for 30 minutes. The mixture was partitioned between EtOAc and sat NaHCO3 solution. Aqueous layer extracted with EtOAc ×3. Combined extracts dried and evaporated. Residue purified on a 12+M horizon column eluting with Pet Et2O to 60% EtOAc/Pet Et2O. Solvent evaporated under reduced pressure to afford the title compound in quantative yield.

Aufarbeitung

  1. customThe mixture was partitioned between EtOAc
  2. extractionAqueous layer extracted with EtOAc ×3
  3. customCombined extracts dried
  4. customevaporated
  5. customResidue purified on a 12+M horizon column
  6. washeluting with Pet Et2O to 60% EtOAc/Pet Et2O
  7. customSolvent evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c41fd2e5757e4c21a37ccafa1ecd2610
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07683056B2

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