Stannous chloride dihydrate → 4-(4-Pyridin-2-yl-[1,2,3]triazol-1-yl)-phenylamine

HRID 1924924Notes

Reaction equation

HRID 1924924 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:12]=[N:11]2)=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl>C1COCC1.CCO>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:13]1[N:12]=[N:11][N:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 590229972-[1-(4-Nitro-phenyl)-1H-[1,2,3]triazol-4-yl]-pyridine

Product 1

HCID 590231334-(4-Pyridin-2-yl-[1,2,3]triazol-1-yl)-phenylamineYield 31.4%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a stirred solution of 2-[1-(4-nitro-phenyl)-1H-[1,2,3]triazol-4-yl]-pyridine (0.149 g, 0.556 mmol) in 1:1 THF/EtOH (8 mL) is added tin (II) dichloride dihydrate (0.439 g, 1.95 mmol) and the mixture is stirred at room temperature for 22 hours. The solvent is removed in vacuo and 2N NaOH (3 mL) added to the residue. The mixture is stirred for 1 hour, diluted with water and extracted with DCM (3×40 mL). The organic layers are dried over Na2SO4, filtered and evaporated to give a crude product purified by Isolute FlashSilicaII Cartridge chromatography, eluting with 98:2 DCM:MeOH. The fractions containing the title compound are combined and evaporated to afford the desired compound as a yellow solid (41.4 mg, 31%).

Workup

  1. customThe solvent is removed in vacuo and 2N NaOH (3 mL)
  2. additionadded to the residue
  3. stirringThe mixture is stirred for 1 hour
  4. additiondiluted with water
  5. extractionextracted with DCM (3×40 mL)
  6. dry with materialThe organic layers are dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give a crude product
  10. custompurified by Isolute FlashSilicaII Cartridge chromatography
  11. washeluting with 98:2 DCM
  12. additionThe fractions containing the title compound
  13. customevaporated

Sources & evidence

ORD record
ord-8ff26fa2c3fc44e88d3f5470ff6a7ac1
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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