Iodine → 4-[3-(Hydroxymethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzonitrile

HRID 1678779Notes

Reaction equation

HRID 1678779 reaction equation
[OH:1][CH2:2][C:3]1[N:15]2[C:6]([C:7]3[CH:8]=[C:9]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:10]([C:16]4[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=4)=[N:11][C:12]=3[CH:13]=[CH:14]2)=[N:5][N:4]=1.[NH4+:30].[OH-].II>C1COCC1>[OH:1][CH2:2][C:3]1[N:15]2[C:6]([C:7]3[CH:8]=[C:9]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:10]([C:16]4[CH:17]=[CH:18][C:19]([C:20]#[N:30])=[CH:22][CH:23]=4)=[N:11][C:12]=3[CH:13]=[CH:14]2)=[N:5][N:4]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14923Ammonium HydroxideHCID 594728804-[3-(Hydroxymethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzaldehyde

Product 1

HCID 594729444-[3-(Hydroxymethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 14-2 (0.4 g, 1.1 mMol) in anhydrous THF (15 mL) was added 3 mL of concentrated NH4OH. The solution was then treated with iodine (0.4 g, 1.6 mMol) followed by stirring at room temperature overnight. The reaction was quenched with saturated sodium thiosulfate solution (20 mL) and the product was extracted into ethyl acetate three times. The combined organic layers were washed with brine, dried with Na2SO4, filtered and concentrated in vacuo to yield 15-1 as a tan solid. Mass (M+1) calculated: 378.135 observed: 378.1345

Workup

  1. customThe reaction was quenched with saturated sodium thiosulfate solution (20 mL)
  2. extractionthe product was extracted into ethyl acetate three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d26b95519e4e4f3aa7dfa154d66d8883
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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