Pyridine → 2-(2,4-Difluorophenyl)-1-{3-[(e)-4-(2,2,3,3-tetrafluoropropoxy)styryl]-1h-1,2,4-triazol-1-yl}-3-(1h-1,2,4-triazol-1-yl)-2-propyl dihydrogen phosphate

HRID 1006653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1006653
[P:1]([O:19][C:20]([C:49]1[CH:54]=[CH:53][C:52]([F:55])=[CH:51][C:50]=1[F:56])([CH2:43][N:44]1[CH:48]=[N:47][CH:46]=[N:45]1)[CH2:21][N:22]1[CH:26]=[N:25][C:24](/[CH:27]=[CH:28]/[C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]([F:42])([F:41])[CH:38]([F:40])[F:39])=[CH:31][CH:30]=2)=[N:23]1)([O:11]CC1C=CC=CC=1)([O:3]CC1C=CC=CC=1)=[O:2].Br[Si](C)(C)C.N1C=CC=CC=1.[OH-].[Na+].S(=O)(=O)(O)O>C(Cl)Cl>[P:1]([OH:11])([OH:3])([O:19][C:20]([C:49]1[CH:54]=[CH:53][C:52]([F:55])=[CH:51][C:50]=1[F:56])([CH2:43][N:44]1[CH:48]=[N:47][CH:46]=[N:45]1)[CH2:21][N:22]1[CH:26]=[N:25][C:24](/[CH:27]=[CH:28]/[C:29]2[CH:30]=[CH:31][C:32]([O:35][CH2:36][C:37]([F:41])([F:42])[CH:38]([F:40])[F:39])=[CH:33][CH:34]=2)=[N:23]1)=[O:2]

Komponenten

7

Edukt 5

HCID 1049PyridineHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 76113BromotrimethylsilaneHCID 22266795Dibenzyl 2-(2,4-difluorophenyl)-1-{3-[(E)-4-(2,2,3,3-tetrafluoropropoxy)styryl]-1H-1,2,4-triazol-1-yl}-3-(1H-1,2,4-triazol-1-yl)-2-propyl phosphate

Produkt 1

HCID 222667972-(2,4-Difluorophenyl)-1-{3-[(e)-4-(2,2,3,3-tetrafluoropropoxy)styryl]-1h-1,2,4-triazol-1-yl}-3-(1h-1,2,4-triazol-1-yl)-2-propyl dihydrogen phosphateAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of the compound of step (a) (298 mg, 0.37 mmol) in methylene chloride (5 ml) was cooled to 0° C. and then treated with bromotrimethylsilane (254 mg, 1.66 mmol) and pyridine (180 mg, 3.10 mmol). The resulting mixture was stirred at 0° C. for 3 hours and then quenched with water (1 ml) containing sodium hydroxide (96 mg, 2.41 mmol). The mixture was then acidified with dilute sulphuric acid and the product extracted into ethyl acetate. After washing with brine, the ethyl acetate phase was dried (MgSO4) and the solvent evaporated to give the title compound as a pale yellow foam (202 mg, 88%).

Aufarbeitung

  1. customquenched with water (1 ml)
  2. extractionthe product extracted into ethyl acetate
  3. washAfter washing with brine
  4. dry with materialthe ethyl acetate phase was dried (MgSO4)
  5. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ce39226018424f7eb121293056cfc68e
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06790957B2

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