Tributylphosphine → 4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenylamine

HRID 2261746Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2261746
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][OH:15])=[C:12]([CH:16]([CH3:18])[CH3:17])[CH:11]=[N:10]1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23](O)=[CH:22][C:21]=1[CH3:27].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:23]2[CH:24]=[CH:25][C:20]([NH2:19])=[C:21]([CH3:27])[CH:22]=2)=[C:12]([CH:16]([CH3:18])[CH3:17])[CH:11]=[N:10]1

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 178194-Amino-m-cresolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 57443256(1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazol-5-yl)methanol

Produkt 1

HCID 675278794-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenylamineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a 0° C. solution of [2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-yl]-methanol (3.0 g, 10.6 mmol), 4-amino-3-methyl-phenol (2.0 g, 15.8 mmol), and tri-n-butylphosphine (3.2 g, 15.8 mmol) in toluene (30 mL) is added a solution of 1,1′-(Azodicarbonyl)-dipiperidine (4.0 g, 15.8 mmol) in toluene (40 mL). The reaction mixture is allowed to warm to room temperature and is stirred for 3.0 h. The reaction mixture is partitioned between EtOAc (50 mL) and water (60 mL). The organic layer is washed with brine (60 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography (EtOAc/Hexane) to afford the title compound as a solid (2.3 g, 56%). LC-ES/MS m/e 390.0 (M+1).

Aufarbeitung

  1. customThe reaction mixture is partitioned between EtOAc (50 mL) and water (60 mL)
  2. washThe organic layer is washed with brine (60 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to a residue
  6. customThe residue is purified by flash chromatography (EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-255dbde049e6458ab97f759eac6ffc5f
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846960B2

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