Water → HCID 69093881, compound

HRID 2174268Notes

Reaction equation

HRID 2174268 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[Na+].Br[C:9]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[N:12]=[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[N:10]=1.O>CN(C=O)C>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][N:13]1[C:9]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[N:10][C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[N:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 1048PyrazoleHCID 24758Sodium hydrideHCID 69094001HCID 69094001, compound

Product 1

HCID 69093881HCID 69093881, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of pyrazole (1.1 eq) in DMF is treated with sodium hydride (e.g., about 60% w/w in mineral oil, about 1.2 eq) and stirred for about 10 min at room temperature. 2-(5-Bromo-1-(2-fluorobenzyl)-1H-1,2,4-triazol-3-yl)pyridine (I-16, e.g., 1.0 eq) is then added. The resultant mixture is warmed to about 50° C. and stirred at that temperature for about 1 h. The reaction solution is cooled to room temperature, poured into water, and filtered to yield 2-(1-(2-fluorobenzyl)-5-(1H-pyrazol-1-yl)-1H-1,2,4-triazol-3-yl)pyridine (I-10) as a solid.

Workup

  1. stirringstirred at that temperature for about 1 h
  2. temperatureThe reaction solution is cooled to room temperature
  3. filtrationfiltered

Sources & evidence

ORD record
ord-e549618a3fc543fd942af06f879ffc8c
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

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