StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Phenylboronic Acid → 1,1,1-Trifluoro-4-(4-methoxybiphenyl-3-yl)4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol

HRID 400674
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 400674
Br[C:2]1[CH:3]=[CH:4][C:5]([O:28][CH3:29])=[C:6]([C:8]([CH3:27])([CH3:26])[CH2:9][C:10]([CH2:16][C:17]2[NH:25][C:20]3=[CH:21][N:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)([OH:15])[C:11]([F:14])([F:13])[F:12])[CH:7]=1.[F-].[K+].[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1.C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:12][C:11]([F:14])([F:13])[C:10]([CH2:16][C:17]1[NH:25][C:20]2=[CH:21][N:22]=[CH:23][CH:24]=[C:19]2[CH:18]=1)([OH:15])[CH2:9][C:8]([C:6]1[CH:7]=[C:2]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:3]=[CH:4][C:5]=1[O:28][CH3:29])([CH3:27])[CH3:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 469390184-(5-bromo-2-methoxyphenyl)-1,1,1-trifluoro-4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol

Produkt 1

HCID 469390191,1,1-Trifluoro-4-(4-methoxybiphenyl-3-yl)4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-olAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845
palladium(II) acetate
Katalysator
HCID 8028TetrahydrofuranLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-(5-bromo-2-methoxyphenyl)-1,1,1-trifluoro-4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol (188 mg, 0.4 mmol), Pd(OAc)2 (9 mg, 0.04 mmol), DCyBPP ((2-dicyclohexylphosphino)biphenyl, 28 mg, 0.08 mmol), and KF (93 mg, 1.6 mmol) in 3 mL of THF at room temperature was treated with phenylboronic acid (74 mg, 0.6 mmol). The reaction mixture was microwaved for 20 minutes at 120° C., cooled to room temperature, diluted with 20 mL of ethyl acetate and filtered through diatomaceous earth. The filtrate was washed with 5 mL of 1.0 M aqueous sodium hydroxide solution, water, and 5 mL of brine. The organic phase was dried over magnesium sulfate, filtered, and the solvent evaporated in vacuo. The residue was purified silica gel chromatography to provide 75 mg (40% yield) of the title compound as a white solid.

Aufarbeitung

  1. customThe reaction mixture was microwaved for 20 minutes at 120° C.
  2. filtrationfiltered through diatomaceous earth
  3. washThe filtrate was washed with 5 mL of 1.0 M aqueous sodium hydroxide solution, water, and 5 mL of brine
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-258ee877ac684ea9800514fd4cf18580
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08741897B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion