Sodium hydride → tert-butyl {5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetate

HRID 2074119Notes

Reaction equation

HRID 2074119 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]2[NH:11][N:10]=[C:9]([C:12]3[N:13]=[N:14][N:15]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)[CH:16]=3)[CH:8]=2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:11]([CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[N:10]=[C:9]([C:12]3[N:13]=[N:14][N:15]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)[CH:16]=3)[CH:8]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 670923504-[5-(4-fluorobenzyl)-1H-pyrazol-3-yl]-1-(4-methoxybenzyl)-1H-1,2,3-triazole

Product 1

HCID 68360285tert-butyl {5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetateYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[5-(4-fluorobenzyl)-1H-pyrazol-3-yl]-1-(4-methoxybenzyl)-1H-1,2,3-triazole (19.0 g, 0.052 mol) in anhydrous THF (100 mL) was added NaH (2.6 g, 0.06 mol) at 0° C. and the mixture was stirred at RT for 2 hours. tert-butyl bromoacetate (12.5 g, 0.057 mol) was then added at 0° C. and the mixture was stirred at RT for 2 hours. The mixture was evaporated and the residue was purified via column chromatography (silica gel, EtOAc/Petroleum ether 1:1) to yield the title compound (20.0 g, 76.0%) as a yellow solid.

Workup

  1. stirringthe mixture was stirred at RT for 2 hours
  2. customThe mixture was evaporated
  3. customthe residue was purified via column chromatography (silica gel, EtOAc/Petroleum ether 1:1)

Sources & evidence

ORD record
ord-2649e3f9377849f1b649f0d48b770429
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

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