Benzaldehyde → 3-(4-fluorophenyl)-1-methyl-alpha-phenyl-4-(4-pyridinyl)-1H-pyrazole-5-methanol

HRID 489936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 489936
[Mg].Br[C:3]1[N:7]([CH3:8])[N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:4]=1[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.[CH:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:5]2[C:4]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:3]([CH:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[OH:29])[N:7]([CH3:8])[N:6]=2)=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 5462224MagnesiumHCID 22037579HCID 22037579, Verbindung

Produkt 1

HCID 220376773-(4-fluorophenyl)-1-methyl-alpha-phenyl-4-(4-pyridinyl)-1H-pyrazole-5-methanolAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To solid magnesium (60 mg, 5 mmol) under nitrogen was added a solution of 4-[5-bromo-3-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]pyridine (450 mg, 1.35 mmol) (prepared in accordance with Example A-214) in tetrahydrofuran (7 mL). The mixture was heated at 40° C. for 2 hours. Benzaldehyde (1 mL) was added. The mixture was heated to 45° C. for 2 hours. It was quenched with HCl (10 mL, 1N) and washed with ethyl acetate. The aqueous acid layer was basified and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over MGSO4, filtered and concentrated to give a residue. The residue was purified with a silica gel column to give the title compound (59 mg, 12% yield). MS: m/z=360 (M+1); 1H NMR was consistent with the proposed structure. Anal. Calc'd for C22H18N2OF.0.6EtOAC: C, 71.1; H, 5.6; N, 10.2; Found: C, 70.9; H, 5.47; N, 10.2.

Aufarbeitung

  1. temperatureThe mixture was heated to 45° C. for 2 hours
  2. customIt was quenched with HCl (10 mL, 1N)
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water, brine
  6. customdried over MGSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a residue
  10. customThe residue was purified with a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-13bb6697c9674ccd885caccc4996b6dd
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06979686B1

Notizen zur Reaktion

Wird geladen…