Sodium Methoxide → HCID 68296408, compound

HRID 631882Notes

Reaction equation

HRID 631882 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=2F)=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][O-:24].[Na+]>C(Cl)Cl.CO>[CH2:1]([N:8]1[C:12]([C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=2[O:24][CH3:23])=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 68296411HCID 68296411, compound2×

Product 1

HCID 68296408HCID 68296408, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-Benzyl-5-(2-fluoro-6-nitrophenyl)-1H-tetrazole (Intermediate 18, 0.3 g) was dissolved in DCM (4 mL) and a solution of sodium methoxide in methanol (20%; 2 mL) was added. The mixture was stirred for 4 hours and then the solvent was removed by evaporation under vacuum. The residue was dissolved in ethyl acetate and washed with 1N hydrochloric acid and then brine. The organic solution was dried with sodium sulfate, filtered and the solvent was removed by evaporation under vacuum. The residue was purified by flash chromatography on silica, eluting with a mixture of DCM and methanol. The fractions containing the desired product were combined and evaporated to give the title compound as a pale yellow solid (0.14 g).

Workup

  1. customthe solvent was removed by evaporation under vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 1N hydrochloric acid
  4. dry with materialThe organic solution was dried with sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed by evaporation under vacuum
  7. customThe residue was purified by flash chromatography on silica
  8. washeluting with a mixture of DCM and methanol
  9. additionThe fractions containing the desired product
  10. customevaporated

Sources & evidence

ORD record
ord-3e2822bc585f4353ad698a33f008b831
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Reaction notes

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