Sodium Hydroxide → 6-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-2-amine

HRID 2174281Notes

Reaction equation

HRID 2174281 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[N:12]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][N:17]=3)[N:10]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+:27].[OH-].[Na+]>C(O)CO.O1CCOCC1.[Cu-]=O>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:10]1[C:11]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[N:12][C:8]([C:6]2[N:7]=[C:2]([NH2:27])[CH:3]=[CH:4][CH:5]=2)=[N:9]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 867132002-(3-(6-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)thiazole

Product 1

HCID 690942396-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-2-amineYield 69%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 22419261Ethylene glycol dioxaneSolvent

Procedure

To a suspension of 2-(3-(6-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)thiazole (I-19) and copper(I) oxide (0.2 eq) in ethylene glycol-dioxane (4:1) in a sealed tube was added ammonium hydroxide solution (˜29% in water, ˜30 eq). The resultant mixture was warmed to 100° C. and stirred at that temperature for 24 h. The reaction solution was cooled to rt, poured into 1N NaOH solution and then extracted with EtOAc. The organic phases were dried over Na2SO4, filtered and conc. The crude product was purified using SiO2 chromatography and an appropriate gradient (EtOAc/hexanes) to give 6-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-2-amine as a white solid (I-14, 69% yield).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customconc. The crude product was purified

Sources & evidence

ORD record
ord-eeea2319a5d741a691d8263b50267465
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

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