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 1006653Notes

Reaction equation

HRID 1006653 reaction equation
[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]

Participants

7

Reactant 5

HCID 1049PyridineHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 76113BromotrimethylsilaneHCID 22266795HCID 22266795, compound

Product 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 phosphateYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-ce39226018424f7eb121293056cfc68e
Source dataset
uspto-grants-2004_09
Patent number
US06790957B2

Reaction notes

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