2-Iodophenol → HCID 86668768, Verbindung

HRID 533543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 533543
[CH3:1][C:2]([S:30]([CH3:33])(=[O:32])=[O:31])([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][CH:16]=1)[C:3]([NH:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)=[O:4].Br[C:35]1[CH:36]=[CH:37][C:38](=[C:41]2[C:46](=[O:47])OC(C)(C)OC2=O)NC=1.IC1C=CC=CC=1O.[F-].[Cs+]>C(OCC)(=O)C.O.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.O1CCOCC1>[OH:47][C:46]1[CH:35]=[CH:36][CH:37]=[CH:38][C:41]=1[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][C:2]([CH3:1])([S:30]([CH3:33])(=[O:32])=[O:31])[C:3]([NH:5][O:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)=[O:4])=[CH:20][CH:19]=1

Komponenten

9

Edukt 4

HCID 107842-IodophenolHCID 25953Cesium fluorideHCID 574434985-(5-Bromopyridin-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 764453942-methanesulfonyl-2-methyl-N-(tetrahydro-pyran-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-butyramide

Produkt 1

HCID 86668768HCID 86668768, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

To a flask containing 2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide prepared as in Preparation Number 3 (150 mg, 0.312 mmol) was added 2-iodophenol (89.3 mg, 0.406 mmol), cesium fluoride (190 mg, 1.25 mmol), water (500 uL) and 1,4-dioxane (3 mL). To this mixture was added Palladium tetrakis (54.3 mg, 0.047 mmol) and the mixture was heated to 115° C. with stirring overnight. The mixture was diluted with ethyl acetate and water. The phases were separated and the crude organic extract was concentrated in vacuo to dryness. The crude material was purified via silica gel chromatography eluting with ethyl acetate/heptanes to afford 4-(2′-hydroxybiphenyl-4-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide as solid. 19.6 mg LCMS: (M−1) 446.3.

Aufarbeitung

  1. additionTo a flask containing
  2. customThe phases were separated
  3. extractionthe crude organic extract
  4. concentrationwas concentrated in vacuo to dryness
  5. customThe crude material was purified via silica gel chromatography
  6. washeluting with ethyl acetate/heptanes

Quellen und Nachweise

ORD-Eintrag
ord-0e2a7591f8aa451d900ec777da5c4044
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853258B2

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