Sodium Hydroxide → 4-(5-(2H-1,2,3,4-Tetrazol-5-YL)(1H-indazol-3-YL))-1,2-dimethoxybenzene

HRID 1353780Notes

Reaction equation

HRID 1353780 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=3)[NH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([Sn]([N:35]=[N+:36]=[N-:37])(CCCC)CCCC)CCC.[OH-].[Na+]>C1(C)C=CC=CC=1>[N:21]1[NH:35][N:36]=[N:37][C:20]=1[C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][N:12]=[C:11]2[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4984872Tributyltin azideHCID 224800333-(3,4-dimethoxyphenyl)-1H-indazole-5-carbonitrile

Product 1

HCID 224798014-(5-(2H-1,2,3,4-Tetrazol-5-YL)(1H-indazol-3-YL))-1,2-dimethoxybenzeneYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-(3,4-dimethoxyphenyl)-1H-indazole-5-carbonitrile (190 mg, 0.68 mmol) in toluene (10 mL) was added tributyltin azide (930 μL, 3.4 mmol). The solution was heated to reflux for 12 hours when 3 N NaOH (80 mL) was added and the solution extracted with ethyl acetate (2×20 mL). The aqueous layer was then acidified with 4 N HCl to pH<1 and extracted with ethyl acetate (3×30 mL). The combined organic layers were dried (Na2SO4) and concentrated to an oil. After remaining at room temperature for 14 hours, the product crystallized from solution to recover, after filtration and drying, the title compound (115 mg, 53% yield). 1H NMR (DMSO-d6) δ 13.4 (s, 1H), 8.70 (s, 1H), 8.04 (d, 1H), 7.75 (d, 1H), 7.54 (d, 1H), 7.49 (s, 1H), 7.12 (d, 1H), 3.85 (s, 3H), 3.81 (s, 3H; ES-MS (m/z) 323 [M+1]+.

Workup

  1. temperatureThe solution was heated
  2. additionwas added
  3. extractionthe solution extracted with ethyl acetate (2×20 mL)
  4. extractionextracted with ethyl acetate (3×30 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated to an oil
  7. customthe product crystallized from solution
  8. customto recover
  9. filtrationafter filtration
  10. customdrying

Sources & evidence

ORD record
ord-1c09ef9472fa476fb97a7b63c8bd0b10
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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